I'll initially handle inbound calls personally until I can iron out the script sufficiently to hand it off to a call center or dedicated salesperson on my team. 

STR'S are here to stay.A massive amount of people prefer to rent a house than a hotel room.When you travel with friends and family it is usually cheaper and you all get to hang together.I have a cabin that sleeps up to 23 people.

I knew a guy that was building his own house and had theft issues, he bought an old trailer and started sleeping out there (with a shotgun I'm sure) and that solved the issue.

I think what you want to buy is 4-5 bedrooms, not 3....numbers start to work better with 4 and even better with 5 bedrooms if you can find one at the right price.Then be willing to sleep on the couch, in the garage, in a tent, in a trailer parked in the drive if you get lucky with roommate #5.Not easy....but doable.You are right on the multifamily side though...very tough from what I see to make any kind of #s work on 2-3-4.I'm guessing in most cases you won't live for free, but heavily subsidize your rent.

If it were me, I would offer him a decent tent, sleeping bag, cash,etc.

If I can make the risk of loss pass to the buyer with a lease that has sufficient terms, can I 1031 exchange the option money?

A network of contacts to ensure sufficient deal flow

As a known entity who CLOSES deals, and has sufficient cash available, I do get deals presented to me with sufficient return/risk to entice me to complete the deal as presented or with little modification.  

One guy is sleeping on an inflatable bed in the living room. 

Your basic insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.