I recommend investing to start in places you can get to an home in a day whether that is a flight or drive. 

One of my favorite Sat. flights used to be going from Portland out the columbia up long beach shoot the approach into Aberdeen then go along the East side of the Olympics to Friday harbor for lunch and then back to Portland in time for cocktail hour.. stunning scenery..

Honestly, I've been getting screwed with some big ticket issues (related to HOAs, selling different properties, continual unforeseen maintenance and costs) and this one really crushed me once I realized it was an actual issue.

It seems easier  to estimate CapEx - I know the big ticket items and roughly how much a new roof is, how much a furnace is, how much an oil tank is, etc..  

I currently have QuickBooks, but I'm not sure if it is possible to incorporate maintenance requests/ticketing, late payment notices, and other landlord specific tools.

That's about all I care about as I hold on to the asset that will in 10-20 years be my meal ticket. 

We do annual inspections and monitor the condition and remaining life expectation of big-ticket items like roofs, windows, HVAC etc 

I have tickets to the 3 day this week and am debating if I will get enough value to justify not working for 3 days.Quote from @Steven Young: I am going to his 3 day mastermind in a few weeks and am happy to hear the positive reviews here.  

i really want to leave this duplex in a solid position when i move out and rent it. i realize that things WIILL break but i just want to make sure the big ticket items are taken care of.

That said, I would also consider beach towns that are out of state but with easy access (ie. a short flight.. say 1-2hrs).