One slow leak in a toilet can run up a VERY high bill (I see it happen enough that I am painfully aware).

D+to C+ Multifamily properties are a pain.

Financing is a pain with the entity, even if Fannie Mae allows single member LLCs.

and now that I have identified the pain point how would you guys approach solving it? 

They're a pain, and the rates are lousy. 

One is a pain to get rent from, and the second pays on time every month, but man oh man is her apt. disgusting.

Those HD/Lowes trips are a pain & a waste of time. 

I can't drop names here but they are super easy to google up I am using my own sub-meters and its royal pain.

@Darren Crawford, Being from San Diego also, I feel your pain.

Forget the "he's hard to read".. just be yourself and respectfully ask straight out.He will see EVERY PLUS and MINUS in any deal immediately:Every tax advantage & disadvantage for him and for you.He may propose adding you to title and you taking over managing the property and splitting the positive cash flow monthly.That will make executing his estate easier in the future.I'm 63 and I can tell you that when you get older it's a pain to be the first contact for tenants in multiple properties-- you never REALLY get to relax or be at peace on vacation.There's always a list of maintenance items to keep up...