Let me break it down based on your scenario and the updated market landscape.Replacement Property and MortgageYou're correct that your replacement property must be equal to or greater than the value of the property sold ($440k in this case) to fully defer taxes.

The most common options used by investors seem to be an LLC or Umbrella Insurance. 

There SOW would usually be - 'I want a remodel done on the kitchen and bath, and add a new bedroom on the left side of the house'...Then I would add items that only a GC would know about or notice, like needing new headers for the openings they want, the elec panel being undersized, or the roof being suspect, etc...Together we would then arrive at a comprehensive SOW.Yes, that is much better scenario.

As far as appreciation, and someone can correct me if Im wrong but looking at all the common markets over an 8 year span, its about the same for all of them.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

FICO is a factor in both scenarios.

That's a common phrase.Real estate investors can get more bang for their buck from their PMs when these folks "think like an investor."

This is fairly common when people want anonymity.

-At the end of the day, if it were me and I was a wholesaler (as opposed to a broker/agent) in this scenario, I would say that "as a courtesy", you can try to help and see if you can sell it to someone else off market, but you should not be expected to do a due diligence for the buyer, that's their responsibility, and you said from the beginning that you are not knowledgeable on land. 

Only thing better would be initial deposit and then paid in full upon Certificate of Occupancy and punchlist complete.Of course, standard items should also be checked: licensed, insured, willing and able to pull all required permits, reference checks.I would also commonly avoid the cheapest bid you get.