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.  

@Christian Sifuentes the only type of inspectors  I have had issues with are the ones working for BGE.

Yes there will still be exceptional deals to find but there are as many sharks as well.Texas is traditionally not a 'quick buck' market so any new investor should understand their investment goals, life situation and risk tolerance before diving in head first.Lot of my Investors treat Real Estate as a means to diversify their Investment Portfolio and are decades away from retirement, so DFW still works.Again - Do your due diligence and YMMV.