First off...Chris's arcade is simply amazing, He has, hands down, the nicest collection of machines, and valuable machines I have ever seen. He not only puts money into them but a lot of time, effort, and experience. As far as I'm concerned his level is out of my league, plus I lack the compulsive attention to detail that makes his restorations amazing.
I have been doing this for 2 years and been through probably about 30 games, until recently I only had about 1000 net into this, that will go up to 2500, but then hopefully down to having money back out very soon. This is how I look at it.
There are three types of games: Those I need, those I want and those I can flip.
Those I need, I will spend market dollar if I can find them, these are my grails.
Those I want, these are the ones that if I find a great deal on I buy, ie. Black Knight 2000 for 600, nice Ms pac for 300.
And those I can flip, these are the ones that are frankensteined to the point where multicades only makes sense. I won't buy one of these for more than 150, most come between 50 and 100, and to me the monitor is worth 50(esp in Hawaii)
But as someone earlier said, only buy what you would keep, so I don't buy flips that I wouldn't be happy keeping once I'm done, and I build to my standards, not the cheapest I can for an extra buck or two. That way if they don't sell I'm not dropping my prices to move things. I also, many times, build to order. By having a top quality machine around, people are willing to order on and make deposits.
I supported buying most of my games by building and selling multicades, or fixing pins for people. The other things I've been doing lately is fixing up someones machine for them in exchange for their other machines. I just traded a 465 in 1 installed into a 1943, for a Ms. Pac, Klax, and Astron belt, seems like a crazy deal but this guy lives in hawaii, loves 1943 and his wife told him he had to down size.(Crazy because he has a new cp, board, coin door, and bezel for Ms. Pac) Anyhow that's my strategy briefly, and it's worked so far, been stressful, and there is not accounting for the sweat equity, but that's the fun part...right?
Oh one last thing, don't down play bargaining. A little strategy, although obnoxious, that has worked for me, is telling the person "This machine is worth x to me", then when they start going on about how great it is, I say "I'm not arguing with you about what you think it's worth, it's worth this much to me, if my numbers don't match yours, that's fine I wish you luck with selling this machine" I don't debate value, I tell them my value of it, and if I start bargaining, it always means I'm willing to walk, and will.