This suggests you plan to keep the condo after you move in with fiance and even after you get married.   

And your $50000 - $56000 (or maybe $62000 with 2 properties) at the end of the year into a 3rd property.3) If you're using conventional mortgages, I think you'll max out at 10, although if you're married, I think you can do 10 in your name alone and 10 in her name alone. 

I'm married with 3 kids, my name is Darcy Maiangowi.Me and my wife have spent the past year rebuilding our credit from 450 to almost 600.

They plant roots, marry, have kids and soon neighborhoods that were once run down are now the place to be.

It sounds like you're not very vested in succeeding with rentals, and when you marry that with the fact that you have some tough rentals to manage, the outlook doesn't sound good.

I'll also mention, we've recently had my 18 year old sister live with us and a couple of friends/a married couple for a few months.

34 married with one 2 year old with more to come hopefully.

@David Krulac is an expert on 1031's maybe he can help.IRS pub 523 allows you claim 250k or 500k (if married) on gains made on a house if you lived in the property for 2 out of the last 5 years. 

Bob should get married to someone that knows how to properly manage money.

Additionally, my wife lived in Haiti for a year and worked in a Hospital as a Physician's Assistant before we got married, and I was involved in water filtration and distribution projects throughout Haiti during graduate school.I am building a real estate portfolio in order to create passive income that will give me the time and financing to volunteer with organizations like eMi without needing to fund raise.Keep up the good work!