I've bought three machines off CL and had to go through each one...it depends who you buy them from. ALL said, "machine is awesome, new rubbers, etc." and NONE of them had new rubbers, the playfields were crazy dirty and things just barely worked...but I paid a fraction of what a shop would charge and have an average of $400 - $800 in each one, fixing them up - but they're AWESOME now, all three of the "working" ones. I just finished the first HS I bought from a local bar/restaurant and it plays just as awesome as it did when I bought it...but looks A LOT better and I'm going to sell it with a FULL description of what's been done, but it won't cost anywhere near the $2,500 the places who "fully shop" them out.
The first HS I bought was my first machine, I took it all apart within 2 weeks of purchase...three months ago. It's nice to finally get it back together but it has to go as I bought a VERY NICE condition HS from a local...and that one's next on the disassembly line.
I'm going to say, if you're mechanically inclined, have at least SOME talent in those hands of yours...and you're a bit "anal" - go for the cheaper machines that still have little to no playfield wear and go from there. Once the playfield is worn (my first HS is) there's no returning it to a condition that'll satisfy most of us...the cabinets can be fixed as long as the artwork hasn't been compromised.
The Checkpoint I just picked up has the artwork on the sides of the backbox "wiped" - it's pure black and I didn't catch that until I had it for a few days - kind of made me laugh when I figured it out - oh well, you don't see it when the machines are side by side anyway...that's how I live with it...but bought the thing for $700 and all it needed was a micro-switch replaced on the ramp so the "speed sensor" worked - playfield is decent, going to strip and clear it probably...in the end, it'll be a beautiful machine (sans backbox artwork) and I won't have a ton of $$$$$$$ wrapped up in it like I do my first HS!!