Boulder, CO
Quoted from LTG:Get your own insurance.
It probably is a good idea to have insurance, but I know many operators who do not.
Quoted from LTG:The harder you make it to break in, the more damage they'll do getting in.
I've never had a problem with break ins, but this is certainly very much dependent on where you operate. Either your pins are doing great and you're doing collections often, or they don't earn much and is it worth spending a lot of time to ensure you don't get $50 stolen? My main location has cameras, and it's not expensive to get a Dropcam if you're worried about it.
Quoted from LTG:As a business. You're an operator or not. No in between like a hobby op.
You don't need to create a separate entity and file taxes separately. It can go on your personal return. You list your income, expenses, and equipment (that gets depreciated). Something like Turbotax will walk you through it.
Quoted from LTG:Where you need to put in everything like pool tables, golden tee's, buck hunter's, juke box, darts, etc. etc.
Although I haven't operated any of that stuff, I'm 100% certain it's easier money than pinball. But then again, it's hard to take pride about owning a Golden Tee. It's not like you're ever going to play it. 
Quoted from LTG:Operator already there. You'd be taking money from him. If he has a contract with the location, forget it. If he lets you in, a good chance your pins will be vandalized.
My two main locations are places where I took over the pins from an existing op because the location wanted a change. Those ops still kept doing the non-pins. I've never had any problems. YMMV.
Quoted from LTG:Put the work in. Like forget spending time with your family. You are on call 24/7. Burglars and fires don't have set hours. Just sitting down to dinner and location calls, haul your butt over there before they throw the game out back.
Sorry to take a harsh stance, but this is complete bull. Yes, put the work in. No, you are not on call 24/7. Don't sleep with your phone next to your head. Get a message about something being wrong? Go fix it as soon as is reasonable. Don't excuse yourself from your day job for a fix. Don't leave the dinner table...just wait till the kids go to bed.
If you have a location that will throw your game out on the street if you're not there to fix it in an hour, then you don't want that location.
Also, if you know your players, and have contact info on the machines - those are going to be your first point of contact. I have players turn a machine off all the time, and I'm there to fix it before the bar even knows anything was wrong.
Quoted from LTG:Don't forget to go to city hall in the town you are going to do this in and check zoning ordinances, license requirements - may be on you, your business, location, each game. And don't try without. Some cities have huge fines and confiscate unlicensed equipment.
This you should do. Some cities have requirements, others don't. Good to know what is required of you.
There are 100 reasons not to try operating machines, but it's pretty easy to put one or two out and see if you enjoy the experience. No need to psych yourself out with all the possible bad outcomes. Sure, anything is possible, but none of the ops I talk to locally are having enough bad experiences to make them regret operating in the first place.
