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.

You can also ask the title company to offeer a "lean Fee Sheet" meaning "Cut the fat" and reduce the BS fee's.  

I don't think we go super low.

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

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.

I have taken a Dave Ramsey approach to my personal finances so have a pretty low nut.

. - Low-income areas = High cash flow, low equity growth - High-income areas = Low cash flow, high equity growth - Median-income areas = Average cash flow, average equity growthFor me, median to high-income areas are where I like to focus.

Yields in Boston are very low.

Larger are as low as $1.15. 

I would look at people that are handyman over anything else, contractors will be used to getting more money and the amount you would pay them would either be too low, or the they would not conform to your work/company.