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...

@Jesse Bull I stay at Airbnb’s in Woodstock for a few days every summer, so it pains me to tell you that in 2019, the town passed ridiculous laws governing short term rentals. https://www.dailyfreeman.com/n...The new policy mandates that short-term rental owners:• Rent to guests no more than 180 days per year and no more than 26 weekends per year.• Provide guests with copies of local laws regarding noise, fire and safety, as well as a map showing the boundary lines of neighboring properties.• Correct compliance issues within 24 hours of notification by the town.• Register with Ulster County for inclusion on a list of rental properties.• Post a safety/egress plan in a visible location inside the building and on the back of each bedroom door.• Provide the town Building Department with contact information for rental properties that are not owner-occupied.The new policy also states that short-term rental “homes” will be limited to renting out two bedrooms at a time, with no more than two guests per bedroom; while short-term rental “establishments” can have up to five bedrooms available, also with no more than two guests per room.Also, short-term rental sites that are nor owner-occupied will be required to have a designated person who lives within 10 miles who is “available to promptly deal with emergencies” and compliance issues.The Town Board has yet to set a limit on how many short-term rental properties can operate in Woodstock and has not yet established any fees that short-term rental operators could be required to pay.

My CAPEX and maintenance budgets for a partial year 1 and full year 2 were decimated, leading to a lot of unnecessary stress and painful situations.Set aside that money now, and either be glad you did or thankful that it potentially won't be needed.I'm sure John can help you with those estimates, but this is one semi-newbie investor to another with probably the only advice I'd go back and give myself buying my first true rental that I didn't already think about or know.

What a pain it’s been.