However, if the appraiser was referring to the style of house, such as tutor versus mid-century modern versus Cape Cod versus traditional, etc, then yes, that has some merit.

The first was a SFH home that I wanted to buy but didn't have enough Cash to get traditional financing.

2) Given my age (47), goals (cash-flow for retirement; longer-term wealth), and the fact that financing would have to be non-traditional (while I have access to a bit of cash, we are entrepreneurs whose tax returns do not look good in the most recent few years), is considering multi-family my best option? 

The issue i'm running into is that many mortgage companies will not finance condo purchases, even with a sizable down payment.Does anyone have experience in non-conforming lending that would allow me to put 20-30% down on a condo with a traditional 30 year mortgage?  

I assume you are thinking you can borrow the down payment and couple that with a more traditional/conventional type loan? 

Be ready to have a plan laid out in timeline (usually two years before traditional financing and you're saving up funds to make larger down payment during this time or pay cash to sellers directly), who will cover repairs, taxes etc. and it can be great for them to know that you would be taking care of the property as your own now (level of care) because you truly want to buy it at the end terms and exercise the right to purchase. 

I think you may have to get aggressive and find off market properties using estate attorneys, probate attorneys and other non-traditional sources for properties that aren't on the MLS. 

I used the BP calculator and found it to cash flow with the traditional long term lease so I believe it to be a safe fallback in case nightly rentals don't work out for it.

My guess is those looking at 50 to 100k will likely not qualify for traditional lending.

I'd like to try and avoid traditional financing if possible.