Hit your thumb with a hammer if you must inflict pain upon yourself, but don't worry about this "deal".

Snow removal is a pain, and I know some Maine landlords who no longer include it in the rent.

The added commute to work was a pain. 

Well, I had hoped that 2018 would be better for our rentals than 2017, last year was very very painful, but we're not off to a good start. 

Using a software will give you quick access to reporting and compare months, quarter, year and so on.An investment of $200 is nothing compared to the pains you will experience at tax time or even getting a loan.

Many of these neighborhoods have flooded multiple times and, in talking to our insurance company and some of the prospective buyers for our home, FEMA can substantially raise premiums (think 15k year) and substantially drop coverage (eg 10k coverage) for some of these areas that chronically flood.

I guess pain points depend on the purchaser and how much they've dealt with real estate overall. 

You potentially have a tough road ahead of you regardless of the direction you go.It will get more expensive the longer you wait.Sealing a sub floor is cheaper than replacing.Remember if it gets to bad you are at risk of loosing more than just that tenant.Oder has a way of creeping throughout, I would hate to see you have to do more work than on just the one unit.As much of a pain as the eviction process is, getter done.

The hard work, long hours and having your mind occupied with the day to day will numb the pain of your loss. 

It's a HUGE pain in the *** for them if you get it wrong, so... something to keep in mind.