Don't be afraid to try it, I run 26 pinball machines at 3 different locations. I started an area here on Pinside that should help you get ideas and ask questions from fellow operators.

Operating pins on location..grab the Novus & soldering iron

https://pinside.com/pinball/forum/topic/operating-pinball-machines-on-location-club

I have a game at my local bar. I get 100% of profits and tip out the bar back so he keeps and eye out for the machine. It's been a hit with the customers and I like to have a pin there when I have a drink there.

Make sure you don't put a STTNG, White Water or something like that on route. It's much easier to fix a machine in your house then in a dark bar.

Theme makes a BIG difference on location.
I first had a DE Simpsons and people loved it. It was getting well over 100$ a month at 50 cent plays.
I thought the game was tedious and not fun so I sold it. Then I put in a Rocky and Bullwinkle and the people who like pinball love it but it makes way less. 50$ A month.

Try it out.

M

I started routing this year in Massachusetts and I started an LLC to make sure I was covered. I am only in one location right now, but with an LLC, I made sure I was covered and above board. I feel it will also give me less headaches if/when I expand to more locations.

As for machines, theme does make a difference. I started with an Austin Powers b/c it was inexpensive and fun for beginners. High Speed 2 is fairing well, and my World Poker Tour was a hit with the local pinheads, but made about half as much as the Metallica next to it. I'd also suggest getting machines that can accomodate $1 bill acceptors. Quarter jams piss people off and may prevent repeat plays.

I like to change the games up frequently to add variety. I should also note that I am my own best customer, and I like variety.

My machines get a lot of plays so I am in there weekly to clean and make sure everything is working 100%. Keeping the machines 100% will no doubt give you a headache every now and again, but there is something really special about going to collect and seeing that a ton of people have been enjoying the machines you provide.

Good luck!