Many have zero experience with the community and don't understand the culture.

You will not only achieve a status upgrade in the market of RE investing, you are given the opportunity to have the knowledge to back it up.

If you can rehab and refinance (BRRRR) to extract all investment and achieve neutral cash flow you would have infinite return (most of my RE investments have achieved infinite return but the cash neutral has in particular gotten a lot more challenging when the rates rose starting Q2 of 2022).Any money extracted via a refinance is tax deferred. 

I also usually compound the return by reinvesting my payments, so the present 12% fund effectively returns 14.38% which is pretty awesome.  

For the community development dept, you'll need proper plans (architect), site survey, permits, etc. when you're ready. 

I am an investor friendly agent as well looking to start my journey in RE investing.

Fast Turnaround: Unlike long-term rentals, you can cash out quickly and reinvest.

We would probably be looking to reinvest within a 50-60 mile radius of La Crosse, WI.

I assume zero as he would have to reinvest all cash received to avoid all taxes, correct?

Long-Term takes the least amount of time, Short-Term the most.Unless you have the time & discipline for this, SELL.4) If you sell, would it make sense for you to re-invest in other rental properties?