I'm thinking I can later cash-out refinance into a loan (possibly a VA loan) to finance another deal and wrap the new mortgage so as to keep the installment payments in place and avoid hitting my retiring family member with a big fat tax bill. 

Compare the budgets, where is the fat? 

Maybe my analogy was too restricted for all viewers, so try this one… Have you ever tried Telling a fat person that they are fat?

REMEMBER: Pigs get fat, hogs get slaughtered. 

My gut is already too fat, so I hate to heap more responsibility on it. 

Chicago code is that EACH habitable room must be at a SUSTAINED temerature of 68 degrees F during the day and SUSTAINED 66 degrees F at night.

Even if you are holding the cash on the sidelines while you look for a deal, you still are better having access to the cash instead of having a fat balance sheet.

And along the way sell some apartments and pocket those fat commish checks I sold a 5 mil one a few years back and that was a smooth 100k in my jeans for a couple weeks of scouting finding and following it to the close..

The last thing I would want is to have a property break even with no fat to skim as a contingency. 

Save the money for a year or two and start looking for a "fat pitch."