There are a few scenarios where I can see these costs being beyond what you have budgeted for maintenance:~You choose to defer repair of these until the tenant is out of the property~ Your property hasn't been updated in a while and many categories are reaching the end of their useful life.I can see 3 things happening if you are deferring maintenance1.

If you are looking in multiple towns ask how the cost would vary (different fire protection, coastal risks, etc.)

However, the rules vary greatly from state to state and because cities often further regulate the landlord-tenant relationship, it's very important to know the rules for your specific location.

If you plan on renting year round, you want to be mindful of occ. rate as certain areas in FL is not most have seasonality rates that vary during snow bird season and summer timeAnnual Revenue$31,067Average Daily Rate$165Occupancy Rate52%

VRBO for me...their customer support is so much better it's ridiculous....In my experience, STRs are generally cheaper than hotels and you get so much more (but I'm sure this can vary by area). 

Mat,As you mentioned, insurance on the 1-4 family rentals can vary property to property.

@Erica J. it varies so much by property type, construction and geographic area for data to be comparable.

This varies state by state, and I'm no CPA / attorney etc so please take with a grain of salt. 

Does Stessa link to cards and categorize expenses (plus allow the user to edit categories?

This question is open to anyone else as well, I've heard some varying opinions on this and would love to hear some more!