In order to defer all of the tax you must purchase a replacement property that is at least as much or greater than what you are selling for.

Generally, there are more prospective tenants who may behave this way with lower-priced rentals.

Also, the tax benefits of the buy and holds help offset the increased tax consequences of fix and flips.

It is better suited to someone who loves Costa Rica and would like a property that they can spend a few months a year at if they would like and still cash flow after all maintenance and utilities and taxes.  

Local banks typically offer lower interest rates but might require a solid track record and detailed financials.

If you are having that much activity but cannot find the right tenant than you will want to lower the price just slightly to entice better tenants OR you can relax on your qualifications.

We took the reverse action and started lowering asking rents until they moved.I suspect the reason that one property of yours turned quickly is because your asking rent was very favorable vs. local competition. 

They may tell you a certain % but then if you offer significantly lower they might change or retract that number.

I could also see 15% corp tax and the whole no tax on tips thing.

And then buy a few SF homes in good school districts, probably outside of Milwaukee County for lower taxes.