While you visualize what you might do sometime in the future,add columns to the existing porch so the house doesn't look like it might topple over on it's face.

Improving your home well beyond that of your neighbors is a big money loser. You would be better off moving. Especially since this will be much more expensive expensive than you think it will be.

My neighborhood is an eclectic mix of unique homes and located in a desirable area that made it through the market crash nearly unscathed. I live in an area where one house can sell for $110k, and next door/a block over there is a brand new home for $600k. Most homes sell above asking price, bidding wars are common, and the "sold" sign is up usually 2-3 days after the "for sale" sign is put in the front yard. I am not worried about my investment currently. I live within walking distance of a fresh food mart, I am 5 houses from an elementary school, I am 2 miles from a major teaching hospital with a level 1 trauma center that employs over 10k people, and I am located within the corridor of the two major expressways that can get you anywhere in the Metro area or Downtown within 15-20 minutes. I am not planning on selling my home - it will at the very least become a rental and make me top dollar should I ever want to move.

To address the roof issue, though - that is not a porch of any kind on the front of my home and columns would look weird - it is as though they started to make a porch and stopped about 18 inches out from the house (which is why I wanted porch ideas). I want this to be one of my first projects, but I am having problems finding bungalow homes with the "4 walls & a pyramid roof" style my home is, plus I want the porch to be able to work design wise with any second-floor master suite addition that I will hopefully add to the next big project. Is this style of bungalow called something else (beach bungalow, craftsman bungalow, etc.)? I am not familiar with home sub-styles; just the models most homes are these days.

Hire a local architect if you are not worried about putting 200K into a 120K home. The porch idea needs to be integrated into the master idea. They are not separate eyes and lips stuck onto Mr.Potatohead. Structurally, a tear down might be cheaper than what you want to do. Especially if the foundation is inadequate to carry a second floor.

" it will at the very least become a rental and make me top dollar should I ever want to move"

Wow, sounds like paradise!

You will never recoup the cost of adding on.

Yea,it's not often you will find fun projects where rules don't apply then wind up making money despite being your first such project. I believe that's called a win,win.

I wouldn't encourage you to drop $$$ in remodeling that particular house but if you love neighborhood so much, you could keep alert on future bargains and spend money on a "better" house. Don't get me wrong, your house is lovely but you seem thoughtful about how you spend your housing money, hence the suggestion.

as for the price disparity you mention, I doubt the person that bought for $600k wants neighbors who bought at $150k.

@GreenDesigns: Yeah, we have some homes like that in my city. I call them 'housettes'. With 850 sq/ft there can't be room for storage or closets. I knew a single gal who lived in one. She used the 2nd bedroom as a closet / storage. Not worth investing any appreciable money.

It's a weird housing market; I get that most outsiders don't understand (I didn't know until I started looking at homes) regardless of the good investment or bad investment aspect --- I NEED MORE SPACE! I don't mind putting money into my home, even if I only break even - which is what I know will likely happen. However, I need this home to function for me for the next 7+ years regardless. I am single, and that is not going to change in the foreseeable future (even if it does, as I said I currently have two bedrooms and decent storage with the attic & 1.5 car garage). Scratching the build-up, would it be cheaper to build-out off the back of my home and just reconfigure my current layout? My neighbor has a build-out addition and my other neighbor a couple of doors down has a build-up addition (same footprint/layout as my home) - so neither way should be a problem getting approved or supporting the weight of a second floor. I am looking for opinions and ideas to bounce freely between professionals and amateurs on this site who may see or suggest something I have not thought of yet; I do not feel I am at the stage where I want to hire an architect - I want a better idea of what I am asking for before I just throw all this at them. I am ideally trying to get to a three bedroom (even if one is a small marketable nursery/office), 1.5 baths (preferably 2) the cheapest way possible. Again, I am open to and simply looking for design ideas and suggestions - not financial advice on my investment.

AIRBNB?

I like the look of the bungalow, which is why I bought this style of home. There are a couple that I have found that I like and think might work depending on which route I choose for the addition that I so badly need at some point.

I like this because it looks like a craftsman, but without the second story attic room that I am used to seeing in my area. I like the exposed opening above where the roof peaks up; keeps with the flow of the pergola. I do not like the colors, but I like the little bit of stone accent.

I like this one because I think that I can use the existing roof that is built out a little and finish it off with a nice little porch to make my house stand out a little bit. However, my front door wouldn't have the double peek-a-boo windows on either side of the door because my door sits right against the wall in my living room and I think that might take away from the look that this house is going for.

I like this design the most; it would give me an extension to my living space in the summer - I love being outdoors and I like the arch with the pendant light hanging above the door. Instead of white pillars, I would want a nice solid weather resistant wood & maybe some stone accents of some kind (similar to the first photo).

This is a rough layout of my house, please note the measurements are liberal in some places. I am using it to get ideas. The HVAC & HWT is located in the Laundry Utility room, in the area between the 3 walls of the kitchen wall, bedroom 2 and closet wall of the second bedroom. I hope this helps for any redesign ideas that people may have. Also, I believe that the home inspector stated that the roof was almost fully supported by the outer walls and the expansive middle wall running between the front & back fo the home (LR/Master, Hallway/Kitchen, Bedroom 2/Laundry Utility Room).