Welcome! I bought my first pin about 6 months ago, and like you I tend to be very deliberative and rational about decisions like this. My main piece of advice would be, don't be so deliberative and rational about this! The #1 criteria should be buying a game that you're excited about. Always remember that if you do your market research and make sure that you're getting a decent price, you always have the option of turning around and selling it for about what you paid for it if it doesn't work out for you (as long as it's not NIB). It's also hard to predict exactly what owning a particular machine is going to be like for you. For instance, I went in thinking that I didn't really care much about the theme, but I ended up with one with a theme I like a lot. In retrospect I'm very glad that I did, since a theme that I didn't like would get awfully annoying after awhile.

I agree with the advice about lots of repairs/maintenance being likely on an older, cheaper machine. If that doesn't sound like something you want to get into, spend more like $3-$5k for your first pin if you can. An "entry level" game should be a more expensive one, and then as you get into the hobby and learn more you can tackle needier, cheaper machines.

Something that I did was to make sure I bought from a Pinsider with an established and positive seller's history, since I didn't really know what to look for myself in terms of assessing the condition of the game. That made me a lot more confident that I wasn't getting ripped off or making a huge mistake. In retrospect, it probably wasn't absolutely necessary to go that far, but it certainly made me more comfortable. Partly because I wanted to do it this way, I didn't have one game I was looking for, but rather a list and once I saw one from a good seller at a good price I was ready to jump on it. As others have said it's important to be able to move quickly when the machine you want gets listed.

One last thing is that there are certain games that are highly sought after, and though they are usually great games, they tend to not be good value for the money. One of those on your list is Funhouse- great game, but you can get one that's almost as good for a couple thousand dollars less. That said, if you find yourself really wanting a Funhouse, go for it. Good luck!