I know you will hate me for this, but please understand my view point. I am an old house LOVER! I also spent twenty years as a banker trying to talk people into understanding that their future home purchase had to be about love....and practicality. When you are in love with a house you think that the fact that it slapped around the last owners was likely because they were bad owners...they probably deserved it because they didn't do the maintenance you would do to keep it in check. You justify the little issues like the third eye as something minor instead of realizing that a third eye is not actually a normal thing and will require some seriously expensive custom lenses. You turn a wet basement into a couple puddles.... Ten years,..no lets make it five if you get the house....if you find that my pessimistic attitude was totally incorrect and your home turned out to be perfect beyond compare...please tell me I am wrong so I can learn a lesson. But if on the other hand my gazillion years of trying to make people understand that they should buy a home they love....but should equally involve their brains and heart in the equation turns out to make some sense in your potential chris brown like situation.....well be sure to share that valuable experience as well so that others can learn from you...and make light of your experience because "that will never happen to them". I tried to buy the egg and I farm as a young wife ohhhhh so many years ago thinking that a house with walls falling down and a tree growing in the living room just needed our tender and inexperienced care to bring it back.....the bank laughed...thank god!

It's very likely doable. Once you get moved in I'd start looking at options for windows and contact a few companies to come out and inspect what you want done. This isn't something you are going to be able to price by making phone calls. When you talk to contractors be sure to ask lots of questions about the experience of the individual who will perform the work and get some references of some similar jobs.

Have you checked your setbacks? Could you convert the garage to extra bedrooms and then add an attached garage in front of that (closer to the street). I understand your dilemma. We live on a suburban lake in a large metro. We bought a house when we moved here with three beds (2 were tiny) on the main floor and a walkout basement on a lake. When our family was growing we were trying to find solutions to stay in that house but get another bedroom on the main floor. We couldn’t build toward the lake which would have been the cheapest and easiest way to make an addition. Adding on a second story would be $$$ and we were seriously looking at gutting the existing 3 beds and two baths and pushing out toward the street to make 4 beds and two baths. It would have been a long drawn out process and cost a lot. It was cheaper for us to pack up and move to a different house on a different lake (in the same suburb/zip code) that already had 4 bedrooms on one floor. Ironically the owners previous to the guy we bought from had converted the attached 3 car garage into a great room on the main floor and amazing master suite on the second floor (originally two story house had just 3 beds upstairs) and they went bankrupt on the addition. We were so fortunate to find a house with the 4 beds on one floor. We didn’t think we wanted to move but we are so glad we did.

@Virgil - Great questions. I don't see us building a fancy deck, just something that matches the house (beach style with hip roof, hardy board siding). Where could I do some research on building materials? For option 1, I would imagine a deck like this one, [https://www.houzz.com/photos/32nd-street-craftsman-exterior-los-angeles-phvw-vp~209718[(https://www.houzz.com/photos/32nd-street-craftsman-exterior-los-angeles-phvw-vp~209718). For option 2, I would imagine a deck like this one, [https://www.houzz.com/photos/630-b-beach-style-exterior-san-diego-phvw-vp~90504781[(https://www.houzz.com/photos/630-b-beach-style-exterior-san-diego-phvw-vp~90504781). For option 3, I would imagine a no-deck-look like this one, [https://www.houzz.com/photos/incredibly-green-home-of-chevy-chase-craftsman-exterior-seattle-phvw-vp~360047[(https://www.houzz.com/photos/incredibly-green-home-of-chevy-chase-craftsman-exterior-seattle-phvw-vp~360047). @kudzu9 - I live in San Diego (yes, I know, expensive). I wish it was like asking, "How much does a new car cost?" because I could go online and figure that out in 10 minutes. And I'd know that I'd never have to pay more than the sticker price! @Sophie - Thankfully, you're not the CFO of my company. ;) $68k is a trip around the world with my family.