Thanks for the feedback, Astro.
I haven't drank any wine for the past 2 days now, so I'm doing better on that front at least. But as far as everything else is concerned, I'm beginning to try to think about where my boundaries are with everything.
As for the house, I closed on it at $62k. I'm now at around $49k with my mortgage. So far, I think I've spent about $36k on basement work (replaced 2 entire sides, added new footing with both sides along with 2 lengths of perimeter drainage, with an additional sump pit, and removed a lot of old wall and foundation stuff). I think I've spent at least $8k on various yard drainage and sump exit line installs. And this spring, I'm planning on spending around $3k to reroute both sump pump exit lines out through one of the new basement walls to have a shorter connection to the city drain line, which will also stop noises and vibrations whenever they kick on, too. I'm also hoping to spend only around $2k to rework an i-beam that was installed from the prior basement wall work to reinforce and better secure it (to also help level some flooring above, too). With the math, I'm basically closing in on spending more on all this than the house is worth, but the problem is that if I don't do these things, I worry about being able to resell it if and when the time comes.
I haven't even upgraded the HVAC yet, which is probably more than 30 years old, and the system I plan on getting installed for that will be around $9-10k. (But this should have some pretty good return for the resell worth.)
The good news in this is that the car and truck are paid-off with the truck's new engine having a 3-year / 100k warranty. I also have a backup engine in the garage for the car if anything ever happens to it. It'd still cost a good penny to install it, but not as much as it would if I didn't have the engine, ya know?
So where's my breaking point in all of this? I've been thinking a lot about that lately. I know I don't want to rent anymore because the places I've seen around where I live to rent are places I wouldn't do well in... But since I don't have any money to buy a new home, well, I think I'd finally give up if I was *forced* to replace anymore basement walls. It'd be one thing if I chose to do it at my own convenience as that would be a planned, controlled situation... But it's another if something collapses, etc. So if something dumb like that happens, I think that'd be it for me with this place whereby I'd do whatever I'd need to replace / repair the problem (i.e. - take out a loan, arrange things with contractors, etc.) but once everything would be completed, I'd finally sell this place and leave. I don't think anything in the basement is close to doing something like that... The closest thing is the i-beam thing, but I'm planning on getting that fixed this spring. I do have some cracks in the old footings, but the worst are in the crawlspace I have that has plenty of support around it from the crawlspace area (and cracks in old footings of older homes isn't something to get too worked-up over in most situations as long as it's not major load-bearing or retaining anything the way a basement wall does). I don't see anything else that's too worrisome with the remaining older walls I have in my actual basement. I don't like the mortar I see in them and it'd be best to one day replace what's remaining, but they don't look like they're going anywhere anytime soon, so structurally, I think it's okay.
But with all this in mind, I'm trying to schedule a time with a separate contractor company south of my location who specializes in these kinds of things to come out and give me an assessment and quotes on things. I'm hoping they put some things into perspective when they come out.