So I may be okay breaking even the first year or two. 

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

That may be the path for a year or two while you figure this out.

Couple, unmarried, two cats, 50k in savings, mid 30s, credit over 780!

I'm also not super optimistic on rents increasing over the next year or two though, especially if we go into a recession.

I am most comfortable with long-term rentals, but I would like to try a flip or two to build my capital.

I am still living in Chicago but plan to move to New York in a year or two.

But again, dedicated crews drive reno costs down.If you can connect with a flipper in your area (quick out your local REIG) and ask to come along when they scope out a job, you will get more from one or two trips than from a dozen books. 

@Mohit Gupta  depending on number of occupants your regular insurance can cover it, read the policy, ours covers two roomers. 

Just my two cents, good luck!