Someone who can structure hard money loans and JV deals.

I'm not sure what laws you think are unclear, but the loan requires occupancy within 60 days.

At most MLS prices, you will not even cashflow $100-150/door with a 20-25% down commercial loan.

What loan would suit the purchaseIn my early 30s, I often wished my parents had told me to buy a house at 18.

Both houses we used Va loans. 

Another issue is these homes have standard 15-30 year loans in my personal name ..... so that is another issue ! 

The debate can be summarized as: For smaller properties trailing financials have many reasons to be wonky, but many believe it is a good signal of transparency and (as @Ben Leybovich points out) this higher variance is exactly why due diligence on the leases can be more important for smaller properties.Line between "commercial" and "residential" seems to be driven mainly by number of units (i.e. is it eligible for FHA loan), even though many commercial banks will underwrite loans on residential properties with fewer than 5 units (especially at larger loan sizes).Is 7809-7815 Franklin a hot deal?

You can use the cash value in the policy as a source of funds for financing, and it is an asset and liquid through withdrawals or loan by borrowing against the cash value. 

We would like to utilize a trust and LLC for this (would be a 5% down FNMA loan) if that matters. 

I guess it would depend on what the lender can offer and their loan specialty.