Even if you had to exceed that, as single you could convert an additional $485,050 above the $63,350 (or $503,350 if married) and you’d only be taxed at the 15% LTCG tax rate (not counting any state if applicable).Each year I’d get my taxable income as low as possible to give myself as much ‘room’ as possible in the 0% tax bracket and convert the max amount possible.

Some months I’ve unfortunately had to pay like $150 out of pocket but I’m Planning on holding long term wise and the let the rental bare fruit later in my life because I’m only 22 and just wanted a base hit or a rental in a great neighborhood.

Will be down in Clearwater Beach next month for a few days and planning on driving some neighborhoods in Pinellas County.

Because I live in a neighborhood that has no crime but it shows up as very high crime because we had two neighbors who would call the cops over each others dogs barking so it lit it up to show it as negative…

Is it wise to buy some units with high cash flow and low appreciation, and others with lower cash flow but high appreciation to diversify my portfolio?  

This could improve your margins.Occupancy Rate: A 60% occupancy rate seems low for Jax Beach, but that is a reasonable conservative baseline. 

For example, areas like Chicago have a strong demand for furnsihed rentals, especially in neighborhoods near medical centers.

Sure you could do a money market or put it in an ETF or something, but this is one of the options where the balance "can't" go down or is extremely low risk while making a decent yield.

Having trouble getting any quotes for a low value SFR (<100k), any leads appreciated

If Chicago, are you already working in any specific neighborhoods?