As always, reccomendations from corporations will typically be profit-motivated, while reccomendations from friends, family, and other investors will typically be genuine and should be given much more weight. 

A good "investor friendly" Realtor is worth their weight in gold.

A good track record for completing escrow will carry more weight than some sketchy proof-of-funds letter from a HM lender nobody's ever heard of.Now, if you do indeed have the funds and consequentially pursue financing for the deal, that's different.

I'm also thinking about offering incentives for good upkeep.

The 50% is basicly upkeep on the house, both big and small.

All 3 of your scenarios out weight everything else.

They said I have to show that it can withstand the appropriate weight per square foot and has proper support.

The fact that the "system" forces you to waste 2 years of you life by taking classes like world history (which you already have taken for the past 10 years anyways), weight training and god knows what else is just beyond me.

These factors weighted against the price and monthly cashflow may mean that the numbers don't make any sense.

A good PM is worth their weight in gold so I'd interview and connect with as many as possible in the market you're looking in.