Hi Amy. I see you're in Kingston, I'm in the Albany area. I suffered the same analysis paralysis when buying my first investment property. I analyzed nearly 100, looked at 20 or 30 and made several offers (including a few that were accepted). After 8 months I finally closed on a very nice Fourplex and now a year and a half later I'm under contract with another 4 Unit for a very attractive price. Here are a few things I learned in my experience thus far:
1. Weed through the bulk of your listings with a simple RTV metric rather than calculating Caps and Cash Flow for each one. Typically each property in a given area has similar taxes and vacancy costs so most things are equal.
2. Use your agent, don't feel bad about making then work for their commission.
3. Remember that you have contingencies and so no offer you make is truly "final".
4. It's said that you can never know too much. When it comes to investing, this is a fallacy. By the time you know everything there is to know about a deal, someone else will already have taken it. At the end of the day you have to accept some risk if you're going to make money.
5. Use as little out of pocket as possible, take advantage of OPM including liberal use of seller's concessions.
6. Good luck!