Bought it as a safe bet thinking it would do roughly $35k annually in short term rents.

I know I want to do this but am suffering from a bit of analysis paralysis trying to figure out if I should jump right in and do small multi-family project or just do a small deal to get my feet wet where if I mess up it wont derail the whole endeavor.

Have you figured out any general numbers yet that you'd be willing to share here?

Now, you need to figure out how to find deals and pay for them.

Instead of shelling out $60K for a $250K deal, maybe some of you can help me figure out (or give referrals) to title companies, etc, or give overall advice how to save me money from this enormous financial endeavor (closing the deal).Thanks!

Since you’re still figuring out where to invest, look for areas with strong rental demand, good schools, low crime, and potential for future growth.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

I am currently unmarried, no kids and recently out of residency with six figures in medical school debt.

I am considering purchasing empty lots priced roughly $10-15K below market value.My plan is to offer owner financing for the land.These lots have water, drainage, and electric connections available, and mobile homes are permitted.The area is experiencing significant development, with the lots surrounded by new single-family homes.I would really appreciate any advice, feedback, or suggestions.Thank you

That's hard to figure out sometime.