I've found it's always best to calibrate around expecting something like the ice cream sandwich episode of The Office. Never feel too much of a letdown this way.
1) I was hooked on day one. Logged on every day, mostly read message boards, paged/chatted with sysops or played door games at first. But very quickly fell down the "hpcva" rabbit hole, which paved the way for the infosec undertones of my career. I'm fuzzy on the program names, seem to remember Telex, Terminate, ToneLoc (a random dialer where you'd scan an entire NPA for interesting carriers).
2) We got a small list of boards from the family friend who helped install our modem, and after you had the first few boards most of the logout screens had a long list of others. There were also lists (by area code) that you could sometimes download from the files section, or some of the grey area ones were traded (usually required NUP/NUV anyway -- new user password/new user voting).
3) Both. Some 20+ node boards were legendary. Some boards were so empty that the sysop would break in after barely giving you time to login because they were so happy to finally see a caller.
4) Drama seemed to matter a lot more. Today it's mostly just drive-by arguing on X or something, and after you exchange unplesantries you move on with your life. On early boards (and into IRC) the communities felt more insular and drama really could divide an entire community and leave lasting marks. Topics were all over the place. Flirting seemed more open, and plenty of fights were just over girls because at the time the female side of tech was extremely unrepresented.
5) How to troubleshoot/fix computers was common. Discussing specific programming languages really bloomed with Usenet and IRC. The t-files on boards that were most interesting to me were about making computers do things they weren't meant to do. Fravia/ORC+ reversing tutorials, or phrack, etc etc.
so how much of a factor is it that safety guardrails may be keeping the current models from achieving higher scores in whatever red teaming benchmarks exist?
Would you integrate with existing POS systems or is this a new one? If a new one do you integrate with some existing hardware for card scans?
I saw the POS systems often have developer/partner programs but at this late stage are they granting those partnerships or is this a gatekeeping system?
Do you have to sell the customer on migrating away from their existing system? How do you convince a massage parlor to migrate from Square? A sushi restaurant away from Toast?
Before here, we looked at WK&T (Kentucky/Tennessee) http://wktelecom.coop/ That looked promising as well.
It was some work to even find these two networks, then finding homes within the service area and trying to find out if they were eligible was the next challenge. Lots of Zillow searches. If the home is pre-wired, they'll probably advertise it as such in the listing. I think the sweet spot (in terms of value) is finding a property that is eligible but hasn't had an install yet. In our case that meant eye-balling the neighborhood maps at a house-by-house level.
To find similar networks in other parts of the US I would start with Zillow searches (for "fiber") or Google searches for state + fiber + rollout, state + co-op + fiber, or state + co-op + Calix. Calix is a popular FTTH equipment vendor. You could also check their (or other vendors) press releases, which they usually issue when they partner with a new co-op. See http://www.ftthcouncil.org/OurMembers
I wish there were a friendlier UX for this. Our search lasted about 2 months. If anyone is interested in my area, email me and I should be able to help by finding properties before they hit MLS, qualifying addresses with the contacts I've made at the service provider/installers, and of course just driving around. It would be fantastic to build a hacker community here.
My fiance and I left Chicago (and $1700/mo) in July for this kind of middle ground. I cross-referenced national fiber optic rollout with low population/rural areas and we found a few acres with 1gbps FTTH in the Lake of the Ozarks area. Our place came with an existing 2 bedroom home with existing private well and electric, all-in we bought for under 2 years worth of Chicago rent.
Our home is/was a bit of a fixer-upper, and it's harder to get help with labor here (it exists, but it's expensive). But one thing I've noticed is that learning plumbing/construction/mechanics has been way easier than learning software. You definitely sweat more though.
Turn-key housing here exists too, it just comes at more of a premium. Also, your social life is obviously impacted. You're probably well-advised to already have a family or s/o (or just are comfortable being alone).
All told, I think this is a great option if you're feeling trapped in your career but have stockpiled some cash. It probably doesn't require near as much money as you might think to make the jump.
For us it's exactly what we needed to focus on our startups without going the traditional VC route. We'd love to see more people going this route. Let me know if I can help.