I'm sorry, but most of that is junk. I just can't see spending $100 on something old and rusty when you can spend $300 and get something that is almost new and higher end. Yes, I know how to work on bikes which is all the more reason for me to tell you to get something new(er). New bikes are so much easier to work on and pretty much all parts are interchangeable and easier/cheaper to find. I'm also going to assume that OP doesn't have the tools and know-how to make the repairs most of those bikes need so that means he's taking it to a bike mechanic. $$$
First of all, newer bikes are
more likely to have proprietary non-interchangeable parts than old ones. I categorically reject your assertion that newer bikes are easier to work on, and even if that were true, it's offset by the fact that they're a lot more disposable (for example, old-school ball bearings can be rebuilt; new-school cartridge bearings just have to be thrown out and replaced.) Take headsets: of the
nine different kinds(!) listed here, at least seven of them are due to the modern phenomenon of proprietary bullshit proliferation. I'll take a conventional threaded headset, which I can fix with nothing more than some grease and a pair of adjustable wrenches (and maybe a stick or something if I need to whack the old races off the head tube), any day!
Second, bike technology progresses slowly -- new bikes aren't generally better than old ones (for example, a fancy indexed grip shifter that fails is worse than an old-school friction shifter that works). Aluminum frames are found on lower-end bikes than they used to be, but that's really about it.
Third, working on bikes is pretty damn easy and requires few special tools.
Fourth, and most importantly,
3x more expensive is 3x more expensive! Even if the OP took that $200 difference and spent it all on tools, and then spent a bunch of time reading sheldonbrown.com and watching Youtube bike DIY videos, I think that is an overall better investment than a $300+ bike that will still need repairs sooner or later anyway (and will have to be taken to the mechanic because the OP has no money left to buy tools then).
Out of the many (way too many) bikes I have, all but one have been bought for $100 or less each, and (except for a $20 tandem I'm rebuilding now) every single one of them was in perfectly rideable condition when I bought them. Hell, my daily commuter is a 25-year-old Specialized Hard Rock mountain bike I got for
free. It was pretty rusty so I took it apart and powder-coated the frame, but that was cosmetic -- all it really "needed" was a $4 spray can of rust converter. It was usable before I disassembled it.
That said, you did run across one reasonable bike that I missed:
https://roanoke.craigslist.org/bik/5524529441.html, a $120 Trek mountain bike. Also, I'm certainly not saying any of the bikes in your list aren't good bikes -- on the contrary; they're better than they need to be! However, IMO there is a clear winner in the $300-400 range, which is the KHS hybrid in
https://roanoke.craigslist.org/bid/5517236653.html. If the OP wants to overpay for a bike then that's likely the one he should overpay for, since at least it doesn't have a suspension fork (which is worse than useless unless you're actually going off-road) and already has smooth tires.
Finally, I'll admit that my "older $100 bike" strategy does work a little bit better if you have a co-op nearby. There's one called "Share Bike" in Roanoke (which may not actually exist; it doesn't seem to have a website) and
New River Valley Bike Kitchen in Christainsburg, about 35 miles down the Interstate -- which isn't ideal, but doable. (I'm spoiled: Sopo Co-op in Atlanta is within a couple miles of my house, which is great.)
