WOW! Fist and foremost thank you all for all the great advise!
I have a pretty good idea of which machines I like, I tend to like games that play fast or have involved rule sets. I play a lot of pinball at the many local places here in the Twin Cities 3-5 times per week at least so I'm pretty familiar with a variety of new and old machines. I'm mechanically inclined and capable so the maintenance and repair doesn't bother me it's actually the part of ownership that I think I'm most interested in besides not having to leave the house to play obviously.
The general consensus defiantly seems like two is the way to go start and as I have been "warned" it'll just be the start.
A couple posters brought up that with all the new games coming out in the next year if I'm patient it might be in my best interest to wait on the JJP pins and get them for less then NIB when people upgrade and I have some more space which I honestly hadn't considered.
If anybody has any suggestions for other DMD or SS machines that would be good I'd love to hear them.
All that being said thank you again everyone!