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.

We couldn't get away without them!

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..  

This started as a nice cabin getaway for the family and turned into a rental.2.5 - 3.5 hr drive depending on where you're coming from and what time you're traveling.You may also want to look into Tannersville, Warwick, Greenwood Lake. 

@Steven Catudal You are free to deduct and will probably get away with it.Do keep in mind if the tenant sues you hold very bad cards for court.

I was really excited to sign up as I think their first student when they started making their rounds in the fall of 2020.

Then you may be able to get away with it. 

San Diego has clear regulations in place, and these areas attract tourists year-round.

But right now, i currently own a SF in KY and am house hacking a duplex in round rock Texas.

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.