Taxes is easiest: seller bought property in 2004 for $260,000 and modest increases in assessed value over 20 yrs.  

I spent 8 yrs in analysis paralysis.

Like the Solo 401K idea but at 71 yrs a little too late to start a business and earn enough salary to grow a Solo 401K for a real estate purchase.

My catalytic converter was stolen there 2 yrs ago while I was working.

The LLC’s could be put into a trust which would negate the tax downsides at the time of my fathers passing (which hopefully won’t be for another 30 yrs or so).

(if I refi and pull out the equity it makes the CoC negative for the next 3-5 yrs)1031 option: sounds good, but I am concerned about finding the right property in the timeframe and my inexperience with this  creates risk.

Not only are prices being pushed and dragged down on all middle and upper inventory, but you can get seller finance 1,000x easier than it's been in literally 30+yrs. 

I have been licensed for just over 20 yrs in 3 states and Florida is my fourth.

After 10 yrs I sold and broke even on both.

The landscaping can't be immaculate while the roof is still 20 yrs old.