I would never do a post-possession without seeing the property unless we keep 80% of the fund on an escrow account contingent upon the seller vacating and the condition not being worse than described.  

I have plenty of clients who go larger multi family units like you described.

@Micheal RobinsonWhat you describe is a mixed use property - retail on the bottom and residential above.

Given what you described (house hacking, FHA loan) a license will have little affect on your success in the first few years.

Based on what you described the LLC is likely the tax-payer on title.

Ray, the strategy you're describing is commonly known as "seller financing" or "owner financing."

I have had mostly great guests, but the few that I've had that were terribly messy (much of what you describe but also smearing pizza toppings on the floor, having an easter egg hunt (I found some of the eggs) with chocolate in fabric and pink maybe egg coloring staining two sets of sheets) and yet were given 5 star reviews from prior hosts.  

A lot is riding on him based on what you described. 

I can't imagine trying to turn it into a full time business unless it is the way that @Don Konipol described it (i.e. volume, lots of staff, good processes to identify and claim funds, etc.).  

Yes you can as long as your father will live in the home as his primary residence and you put enough down to cover your portion of the loan that VA will not guarantee.Here are the VA guidelines for calculating the down payment.VA calculates the guaranty as described in the table below.Step Action1 Divide the total loan amount by the number of borrowers.2 Multiply the result by the number of veteran-borrowers who will beusing entitlement on the loan.There is usually only one veteran borrower, in which case the resultof this Step is the same as the result of Step 1.3 Calculate the maximum potential guaranty on the portion of the loanarrived at in Step 2 (as if that portion was the total loan).Use the maximum guaranty table in section 4 of chapter 3 of thishandbook.4 VA will guarantee the lesser of:• the maximum potential guaranty amount arrived at in Step 3, or• the combined available entitlement of all veteran-borrowers.5 VA makes a charge to the veteran-borrower’s available entitlementin the amount of the guaranty.If more than one veteran is involved, VA divides the entitlementcharge equally between them if possible.