That said, me being the chronic optimist I am, I'm glad I came around to the idea of investing now instead of right before retirement.

There are exceptions if the non-spousal beneficiary is disabled or chronically ill.Previously non-spousal beneficiaries could stretch the IRA distributions over their lifetimes. 

Additionally, she is used to the lifestyle that my dad used to provide while he was still working and she currently spends about $6000-8000/mo (a lot of which is also medical expenses for chronic conditions), so she withdraws from the stock portfolios to supplement current spending.

I'm a therapist, and one of my first interactions was with a home owner with chronic mental health concerns, so I found it fun and interesting, but I'm not sure everyone would feel the same way. 

Are those super cheap properties in ghetto areas with chronic perpetual poverty?  

Another great person wiped out by a chronic drunk driver allowed to keep their license.

Is there such a chronic shortage of skycaps in Nashville that we have to import them from Florida?".

I have CIRS, Chronic Inflammatory Response Syndrome.  

I'm assuming this is the first time this has happened and not a chronic problem?  

I didn't do this with our first purchase, but not too big a deal- one tenant had prepaid, another is on county assistance and they send the check automatically on the first, the third is chronically late with the rent but pays late fees.