However, since the VA loan can be used on multi-unit properties (typically up to 4) buying a 2-4 unit to live in one and rent out the others is a great way to start.

Everything you described is typical and expected of tenants in d and c class areas .

What are they typical terms from small commercial properties right now? 

Usually more flexible, sometimes higher rates, but they'll typically work with you a little more.

As far as the signing then a trustee typically signs "in their capacity", something like this:Joe Smith as Trustee for the Bill Miller Living TrustEscrow probably would not be concerned with "...that these 3 are the owners of the trust?"

Inbox-Junk-Sent typical messaging etc.

Typically, hazard insurance is billed annually.

It's just a phone call away typically.

The HELOC is typically a very quick and easy process with minimal underwriting.  

Pay off the Mortgage and pay off the Heloc with the Rent ($1000) - Expenses ($245), which with simple interest payments comes out to 4 yrs 6 months to have the house free and clear, plus you pay a micro fraction in interest over the less than 5 years.Then part 2 of his strat for advanced investing he called it, he said the typical lifespan of a rental is 7yrs between light rehabs, since you payed it off before the 7yr mark and it appreciated about 10% conservatively, you sell it, and do a 1031 exchange and roll the 100-120k profit into a house that the 60% down payment is within that last rentals sell profit or buy multiples and run the Heloc strat again.