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Jack probably had a military pension or something. Pays well enough, covers health costs so you don't have that as an added expense.
Land is cheap down there. 22+ acres for under $50k in some areas. More or less in others. There's a good chance that much of the wooden things they had were homemade or locally sourced. Also, just owning that much land pays for itself. You can raise livestock, grow (don't know what you can grow in swampland), sell lumber... lot of return on that investment if that's their lifestyle.
Most likely though? The land and house were in the family for generations and they just built up over the years. The wiki seems to think that's the case.
I know this is a month old or more, but it's too fun a topic to resist.
They, or their family in the past, have probably seen at least modest wealth at some point, based on the extent of their resources and certain intricacies of their architecture, definitely including the vast and grand main hall. Generally things that are as grandiose as that would have been when it was new are marks of wealth. That wealth may have been a modest fortune, and it may have certainly dwindled by the time we see the Bakers, since it seems that even when they were happy (as seen in the DLC) their house was falling into disrepair. However, such grandiosity as the main hall represents is almost never seen among those who can't at least be called modestly wealthy.
That said, if size and land were the only factors, a few years ago there was a house for sale somewhere in Georgia that was 10,000 square feet (just barely smaller than the square footage estimated for the Spencer Estate's main house) that cost less than the average middle class home. Less than 300,000 if I'm not mistaken. It looked like it was a perfectly nice home, too, although not nearly as showy and grandiose in design as the Spencer Mansion. It was, as far as I could tell, just because of the location, which was the middle of nowhere and not desirable. So the Bakers could definitely benefit from that, too, since their real estate seems, as you said, less than prime real estate. Maybe, for example, that kind of thing is why they were able to put lots of money into a grand hall, because they were able to spend less than you'd think on all the land and floor space. So, sure, at some point the family probably needed to be wealthy. But maybe only at the bare minimum of what it takes to be considered wealthy.
I'm curious... Their estate is enormous, it's probably bigger than the Mansion in RE1.
Hard to say. The main house in the Spencer Estate is definitely bigger and, on average, more grandiose room for room, and also with more rooms and halls than the main house of the Bakers. The Baker Estate's main house, if you took the main hall away, would be reduced to the size and feel of a big middle class house: The kitchen, the living room, etc., are all quite ordinary or even modest in scale and style. Meanwhile, the Spencer Estate's main house, even if the main hall was taken away, would still be rather big, grand and complex.
The Baker Estate does have more land, though, and more buildings overall. But in terms of mansions (main houses), the Spencer Estate definitely wins. Not only in size, but grandiosity. So in real life, the Baker Estate might be significantly more affordable than the Spencer Estate even if they were both located in the same town, even though it has more land and buildings than the Spencer Estate: Price is often determined by style, grandiosity, and prestige even more than square footage or acreage.
ALL THAT SAID, someone actually went and figured out that the main house of the Spencer Estate, not including the Guardhouse and labs, would cost less than $2,000,000 IF it was in the area of the USA most like Raccoon City. See: https://www.movoto.com/blog/novelty-real-estate/resident-evil/ Since both the Baker's architecture and real estate is likely less "prime" than the Spencer Estate, it's quite possible your dreams of retirement in a Baker-esque Estate for a million or so aren't that far fetched after all.
I thought Jack inherited the land from his family. The house is so old despite a good job maintaining it (pre-infection) and his occupation after the military was a farmer, so that might help shed some light. Farmers sometimes own larges acres of land for harvesting and the like
I'm going to hee-ho down your neck. I'm kidding. Maybe.
It's hard to say. They appear to be at least somewhat well off, though even before Eveline entered their lives the house itself wasn't exactly in pristine condition. Some of the art pieces they owned look like they'd be pretty valuable, though.