But if you're simply planning on reinvesting all to get the best return possible you might also want to think about a diversification exchange where you sell one property and buy more than one.You could buy that smaller land locked piece. 

Areas experiencing growth in population usually see a corresponding rise in housing demand.You should then delve into real estate market trends, examining aspects such as property prices, rental levels, and the average time properties stay on the market.

Usually, lender review the internal photos as well to ensure it can be easily converted back to residential use easily as well.  

I usually do a roommate release form that they both sign.

I did find a couple of investor friendly insurer options on this site so hopefully that bears a couple good options.

Do fee simple homes tend to appreciate at a faster or slower rate than condominiums?

I worry way more about IF they will pay than to what address.

Its better to be in 30 year fixed rate debt that gets paid off from your rentals than being in 100k of CC debt. 

The question you ask sounds simple, only because most people go by “gut feel” rather than any rational thinking.  

For most multifamily, I'm seeing on 30 year amortization to boot.Reminder for the lurkers that this has nothing to do with single family homes, 1-4 unit residential all gets residential mortgage financing, which isn't presently as good as commercial.Odd world where the 8-unit property has a payment that is less than twice as much as the fourplex, even though it pulls in twice the rents, and has less than twice the maintenance expense (the price of the fourplex is likely to be more than half the price of the 8-unit, and more than 1/5th the price of OP's 20-unit, holding constant location etc, but that's another rant for another day).