Or would a DST earn more but considering tradeoffs you still prefer the index funds? 

I want to know what YOU would prefer?

In addition, we have a general contractor who preferred an equity stake in lieu of fees.

What also caught me off guard is you being more concerned about his mail preferences than his recent eviction which would have been a hard pass for most on here. 

Preferably in SW Florida.The property is in Florida so I believe I can have the case filed here?

In addition, we have a general contractor who preferred an equity stake in lieu of fees.

However, we prefer no agents. 

It depends on the bank you are using, most of them prefer long term income (which is more reliable to them and safer) but if you can show proof of income history being used as short term that might help too.

I want to buy a property from an investment perspective, I was wondering which out of these two cities would be preferable in terms of ease of renting (rent per month and the time it takes to rent it out). 

Same builder, same house, in same neighborhood for example could back to a busy main street in the entrance of the neighborhood, could face West where people prefer East facing, be the house that everyone drives by and lights shine in the front windows when you enter the neighborhood, could back to power lines in the back of the neighborhood, could be next to the community pool, could be on a corner with a bigger lot, and a host of other factors go into pricing....not just size.The 3 main sources that most sellers use for size are tax roll, appraiser, or builder's plan.