With so much to do, no right or wrong answers here, other than what Mrs. HCP may want done first. I would breakup the list into two categories, inside and outside. For a house that has been neglected this long; I would start with the outside. Roof does not have much life left Windows, if double pane are probably the old aluminum style, which was a stupid idea because aluminum conducts heat and cold, it is not an insulator. You can reduce your electric bills with good vinyl windows. Porch, maybe a safety issue soon? Paint Doing the outside first will make your neighbors happy, plus it should raise the value of your house. I am not usually up this late, but had a water valve mysteriously break (not frozen, I think the dogs broke it while playing rough, it is low on a wall). Easy fix, I had a spare valve. The hardest part was shutting off the main line valve that has not moved in years. Not what I like to be doing at midnight.
@HCP I need some similiar work done on my houis.e Like the Plumbing. Would love a referral if you like the work your guy does.
Talk to your wife, I can do either a flat fee or a percentage of the insurance money. Make sure that giant SHOE collection of yours is insured. ... Btw, if you don't have your own office in the house you should include that in with the basement remodel. Gives you additional tax deductions. ... 1920 Craftsman, this is the perfect time to secure the house to the foundation if it hasn't been done already.
Maybe install some extra bench seats and a couple of small televisions to make time in the Mrs. HCP line a little more comfortable...
We just finished totally redoing our kitchen, along with having some minor things done around the house. That alone has taken 6+ weeks. And apparently that is record time from what others have told me. I won't reveal the cost but it was obscene (though to be fair, that "speedy" completion is part of what we paid for). We went design/build to reduce the hassle and completion time (and because I'm about like you, skills wise). If you or your wife have the time and temperament to act as "project manager", you can save some bucks, but it will like add a fair amount of time (and further aggravation to an already aggravating process) to the project getting completed. The subcontractors always respond better to the general contractor than they do to the customer. They rely more on them for business than they do for you. As others have pointed out, the very first thing you need to do is prioritize your needs and wants. You didn't say how much you have to spend, but even $100K won't go very far with all the things on your list. Sad but true..... Pay to have it done "right" the first time. Do overs suck.....and it's cheap "insurance". Too, if you "cheap" things, you'll be redoing the whole thing sooner rather than later. Get the best quality you can afford. You pay for peace of mind... If you plan to stay there more than 10 or so years, do it the way YOU (or more specifically your wife) want it, not the way that might make it more marketable. The new owners can fork out to make it the way THEY want it when the time comes. You'll be happier... @riverman is absolutely correct. The new plumbing and electrical should be first priority. The roof second..... As the project progresses, don't be afraid to ask questions, point out things you might not like and/or to ask for changes if you don't like what you see. It's YOUR money. It might make the cost increase but again, peace of mind. Don't be afraid to be a prick where it matters.... Have a good sit down with the missus before the work starts so that you both know this will be a long and stressful process, but that it will eventually end. I cannot stress this enough. Agree to be patient with each other and be ready take a long walk when tempers flare (though hot angry sex also works. Just wait till the contractors leave for the day). Again, this is gonna test your marriage in a bigly way, especially with all you have going. Prior mental prep (and a ton of patience) will insure that the Mrs. HCP jokes don't become reality....... If all else fails, the "burbs" is still a reasonable option.... That all said, congratulations and good luck on your new adventure. If I can answer any questions (an actual possibility) don't hesitate to ask.
My son's house in Eugene, built in 52 is so bad he is going rip it down to the foundation this year. Stud wall of 2x4, aluminum windows, poor wiring, and sagging floor, just too much to fix. Build a new one in place on old foundation raised one block level to create crawl space high enough to work in. Sigh! I think I see my fishing trip to Alaska slipping away.
I recommend a complete attic fire. Something that smolders for a few days while he's visiting you in Bandon so the smoke damage is extensive.
if you have to take it down to the foundation.....just start from scratch....new construction in Eugene is more affordable than it used to be...especially stick frame houses...my ex coworker got one built on her property brand new....set her back about 160k but she got a pretty big house out of it.