Not only can the HOA fine an owner if short term rentals are prohibited, but the city may as well. In our resort area, a short term rental permit is required and the city tightly controls short term rentals. Code enforcement is good. In addition, if the covenants of subdivision disallow short term rentals, the city will not issue a permit. Our current small subdivision does not allow short term rentals and, in 11 years, I only know of one homeowner (a builder) that violated the covenants when he couldn't sell the newly built house during the bust. We turned a blind eye and didn't complain given the circumstances. It turned out not to be a problem. The nightly rental was very high, which kept the usage down, and the house sold at the end of the season. However, although our little subdivision does not allow short terms, they are allowed in neighboring areas, so we do get some short term rentals nearby and have had a few noise issues. The subdivision where we have bought a lot to build does not allow short term rentals and is, for the most part, geographically protected from surrounding neighborhoods that do by green space. The few lots that do back up to another neighborhood were priced lower and still slower to sell. At the annual meeting of the HOA last year, a realtor proxy moved to amend the covenants to remove the short term rental restrictions. The motion was withdrawn when it became abundantly clear that all owners present bought, at least in part, because of the restriction. In resort areas, most folks (or their realtors) already know that you really need to read your subdivision documents closely for this issue. In fact whether short term rentals are allowed is often disclosed in the listing. Some second homeowners may want to rent out their home to defray the cost of ownership, while others want to be away from the bother. With this new phenomenon in other good-time cities, I would expect that a wise buyer there would also check the subdivision documents carefully and also check in with the city.

Wow! What amazing words of wisdom - thank you for all your comments. Just to add a little color on some of the questions that were asked: We had our 3 kids very early, so while they are all off to college now my wife and I are still relatively young (48 & 46, respectively). We are still very healthy and active so we probably won't think seriously about retiring until we are around 55 or so. We have been working with an amazing architect over the past several months. He has been incredibly thoughtful in the design and flow of our house. It is absolutely beautiful. We are in the Midwest so part of the square footage includes basement space. The current design has about 3,600 sq ft on the main floor, 1,600 sq on the 2nd floor and about 2,200 finished sq ft in the basement for a total of roughly 7,400 sq feet of finished space. This does not include the 6-car garage, pool area or outdoor space. The first floor is pretty normal - foyer, kitchen, dining room, great room, master suite w/attached laundry, pantry, mud room, office, music room, lanai and a couple of half-baths. The 2nd floor has 3 bedroom suites and a laundry room The basement is where all the "nice to have's reside" For example, we have a large bar area, wine cellar, TV room, fitness room, dry sauna, play room (for future grandchildren), pool bathroom and a bunch of storage. The basement also walks out to a covered outdoor kitchen area which then flows into the pool area. We entertain a ton so we designed the basement to be very open and spacious. We also have a lake house that is a couple hours away. Honestly, we are thinking of selling it because we are not sure we will ever want to leave this house... although I think our kids will protest quite heavily because they love to go to the lake! The house will sit on roughly .75 acres. We fully intend on outsourcing all the landscaping, yard work and pool maintenance. We both have pretty demanding jobs and don't really want to spend all our free time pushing a mower around or cleaning a pool. No offense to anyone - we have done this work for years, but the older we get the less appealing it is. We are installing a geothermal system that will not only heat and cool the house and provide hot water, but it will also heat the pool very efficiently. We are also going heavy with insulation, windows and doors. We had an energy study performed and all indications are that our utility bills should not be significantly higher than our current house. Long story short - we are going to go for it! Maybe in 10 or 15 years it will be too much for us to handle, but until then we are going to squeeze every ounce of enjoyment out of this house and create some wonderful memories with our family. Thank you again to everyone who contributed to this thread. We are sincerely thankful for your input.

I am having a similar situation with my contractor where he went out of town suddenly right after he demoed my kitchen and then I had to be home and schedule the rest of the work/trades. What should be expected when a contractor included a overhead/profit in their estimate/invoice, but the homeowner was the one who had to stay home and talk to the trades (including scheduling, staying home while people did demo, install, labor, etc.)? I am genuinely curious what this overhead/profit is supposed to cover when the other items on the invoice already included things like labor and materials separately. I know overhead is usually 1.5 of the contractor's cost, but that usually includes things like project management and design. In my case, a lot of the PM and design was on me and I had to miss a lot of work to be home for different people who came over. I also am tempted to bill my contractor for my time -- but, of course, I won't. I would probably just try to talk with him about what I was unhappy with and see if he gives a discount.

Wow, what a wonderful thread. I've enjoyed reading all the posts. Brings back a lot of memories. Until I was 10yo, we lived on a city block with mostly elderly next door neighbors on our block. Two years before I was born, my parents bought a condemned house and remodeled. It became known as the white house with double (navy) blue front doors. Mrs Perry lived in the big house on the corner with tall ceilings and neat staircase. I never got to go upstairs. I would love to go back inside the house today for a look around. She had Mrs Smith take care of her and I would often go visit with her. Mrs Perry was a frail lady in her 90s. Mrs Smith would brush her waist long grey hair and put in a bun. Mrs Perry had a small house in her backyard where her housekeeper/cook lived. I remember going to see her when she was dying. I wouldn't see her much when I was inside the house, but her little house was next to our alley driveway and backyard, so I would talk to her over the fence when she was hanging out laundry. One day the house on the far corner had a fire and we walked down to see the firemen. When my dad got home from work, I ran down the alley to see him, fell and got rocks/gravel in my knee. Still have the scars to prove it. LOL On the other side of us was Mr and Mrs Brooks. They didn't have any children and were heavily involved with their church's orphanage (wasn't in our town). Every Christmas and Easter they would buy book or inexpensive dolls for the children. They would hide plastic Easter eggs in our shrubs with nickels and dimes inside, and/or give us book with coins taped to pages. I would go visit them too. Mrs Brooks had glass shelves filled with vases and glass pieces in front of a pair of windows. She would get down the vase that was filled with small green glass marbles (really filler) and I would play with them. I still have one of the green marbles. Their living room was filled with pretty, but uncomfortable, Victorian furniture. They had a lovely backyard, and Mom often took our photos there. I remember when Mr Brooks was dying we went to say goodbye. We had moved by then. When Mrs Brooks died, their house was given to their church for the minister to live in. When I was in HS, I got to go to a sleepover at the house. Mrs Sullinger lived next door to the Brooks. She was a nice lady with what I now know to be Parkinson's. Her voice shook and her hand trembled a bit. One day she called for me to come over, she had a surprise for me. She had bought several ducklings and a small kiddie pool. Once they grew, she gave to someone with a pond. There were children close by, and at one point my younger cousins lived two blocks away, and my paternal grandparents just past them. So three from same side of the family on one street. Our grandparents picked us up each Sunday for Sunday school, then my parents would come to church. We always had Sunday dinner at my grandparents house. I had lots of first cousins, but most lived out of town. They came sporadically during the year, but always for Mother's Day and Thanksgiving. For K-2nd I went to a small private school (Mrs Carol's). It was in a house in a neighborhood, near an elementary school. When I was in 3rd grade, we were driven to school each morning by my father on his way to the family's furniture store downtown. We often walked home from school. One of my sister's classmates was hit and killed by a train when he was crossing in front on his bike. Later on, the BIL of our gym teacher was killed. I was working in the office and she brought her much younger BIL into the office to tell him his brother had been killed. We later dated for 3yrs during HS. During my HS years, two other students were killed crossing the tracks. These accidents still scare me, and I always always stop, look and listen when crossing. Even if no lights blinking. We moved to a large English Tudor on 3 acres and I went to public school in the 4th grade. I hated that school and cried almost every day. I was extremely shy. Our neighborhood had one way in/out and at Christmas a "tree" was installed on the raft (barrels with wood decking), floated to the center of lake and secured. The strings of lights were beautiful and reflected in the water. I would sit in the front window upstairs and watch cars as they came to see the neighborhood lights. Nights closer to Christmas by the hundreds. A local gardener that developed the Snowflake Hydrangea had greenhouses across the road from our neighborhood. I always wanted to see inside! I could hear, then run upstairs to see the old train blowing smoke when it came to town each year. My maternal grandmother got all her grandchildren tickets one year and I rode most of the trip with my head hanging out of one car. My face and hair were covered in soot. LOL Lots of kids in the neighborhood. We would play tackle football in our "football field" at our house. We had moss battles at the lake. I loved fishing in the lake with my maternal grandfather. They had a house on the river, then at the beach. He was always fishing. I often went roller skating in the driveway or at the rink. Later ice skating each weekend when one was built about 30 minutes away. My mother's brother was in the Navy, and his wife/four children lived with my grandmother when he was in Vietnam. He was Commander of a ship during that time, and a b/w photo of it and him in his uniform always hung in their back hallway. From 5th thru 12th, I went to a small private school my parents helped open. It was small and everyone knew everyone. It was great. My parents grew up with horses, and we bought one that first year. Shortly thereafter, we found out she was expecting. Best BOGO ever! We kept her at a local barn, but after she gave birth there was trouble with a few other horses, so we moved her to the pasture of a lady that worked at the furniture store. I was (mostly) glad when the bull went to slaughter. I joined band in 7th grade when they hired the cutest band director. Played flute and piccolo, and twirled rifle. So lots of HS football games in my past. I missed band so much after HS that I joined the Army Reserve unit and was in the Army Band there for 2yrs before transferring to the MAC (same location). My dad was in the MAC for almost 40yrs. In JH, my girl friends and I would walk or bike miles a day, camped outside without tents, went swimming in the lake or at a club they belonged to. My sister and I wanted a pool, but our dad built an apartment complex near our house and it had a pool, so we went swimming there. I also enjoyed playing tennis at the park and was on the tennis team one year in JH. I spent many hours at the family furniture store, and later another store my dad opened when I was 16yo. Everyone that worked there was family to us. Miss Mary started working for my grandfather at 16yo, and she worked for my uncle until she retired. DH and I went to her funeral with my parents. It was lovely to see her family members we had not seen in decades. She never married or had children, but she loved her nieces and nephews. My grandfather was already a senior when I was born. He would drive to the store each day, sit at his desk reading his Bible. Then go home for lunch, and take his afternoon nap. He died just shy of 99yo. I have two of his hats, and two of my maternal grandfather's hanging in our house. I was close to all of my grandparents and miss them all. Gosh, that was long, but I sure enjoyed revisiting my past I am going to copy/paste, add to it, and email to our children. Thank you for sharing your memories. I truly enjoyed reading them.