I would say that it mostly depends of what you're expecting from the bike.
Getting a cheap bike with work to do, you know you most likely won't daily drive it anytime soon, and it will be few hundreds (sometime thousand) dollars of parts/service plus a lot of your time. For some people, it's fun and they like the hassle (I'm one of them, bought mine for less than $3000 (with 25k miles and a shady past), but I put another $1000+ on top and over one month of work to make it safe). Except that there's a big "luck" factor when you're buying a bike with work to do - because you never know how bad it can be, as previous owners can be pretty rough with these things.
When you're putting a little more money, you know what you're paying for and John's offer is a perfect example. For $5800, you have a fully ready to drive, well maintained and reliable bike. It's hassle free, it fits your criteria and you won't have to spend nights and weekend wrenching it. Just enjoy it.
If you're on the market for a bike to ride, consider putting more money. If you want to work on your bike and have it as a project for your evenings and weekend, keep looking! (and the Ss you're mentioning, if it didn't feel right on the moment, just move on. Plus, you said earlier you don't want anything that leaks, which is understandable).