Side note, the guy is an emotional roller coaster sometimes.

Both are jobs that take time and emotional energy.Beginning both at once, one you are trained in and one you're (learning on your own dime for better or worse) is a big bite.If I were you, I'd buy into a facility with others as Jay recommended, which will add to your net worth and be likely to benefit you long term, and in the mean time stack up liquid cash, as much as you can, and study this business.Or if you want, just go for it and move forward with ether multi-family or single family knowing it's not as time free or risk free as many make it seem.

I will have to work on separating business from the emotional aspect.

After reviewing the applications (and this is probably day 3 of holding the apartment for them because they said they wanted it and then it took another day and a half to turn in their application), she contacted me and said she wanted the rent prorated (I said I had no problem with that) but also that she wanted me to redraft the contracts because "[she] has an emotional support animal.

. ;) Thank you for sacrificing your time, mind, and emotion to serve our country.

Same as #1, I'll never let emotion get involved and purchase on speculation!

@Jesse Lentz, family = emotional decision making = less than optimal investing.But, you already knew that. 

I would definitely not get overly emotional about their financial issues because it is exactly that THEIR issue.

Don't put emotion into it,of you send out 500 letter and don't get any call,send out 500 more and you might get 5 calls .I work as a full time debt collector ,and I realized that rejection is just part of it.

That can’t be undone and is emotional for many people as they age.Also from a financial standpoint this property will not cash flow so you will lose money if problems arise with the property such as needing a new roof, plumbing problems, etc.