The reason for this is that it will make payment more reliable as there has been postal issues in the past.I suggested opening a Chase account as they own my mortgage as they accept photo images of checks which should streamline the process but he is resisting that and has indicated that if I don't do it his way, he will have to raise his fees.I can't help but feel uncomfortable with an arrangement where the property manager wants to deposit all of the rent money into his account as it takes a lot of control away from me and I have a mortgage to pay.

Like you, I was resistant to stop using my spreadsheet and get on quickbooks.

Perfect weather year round.

I did it for the weather.

One problem, taxes work out to be 3x property for investors, insurance are high because it is on the coast and susceptible to weather.

The weather in Florida isn't so great you want to work for nothing!

Over the years, I was able to weather both the financial crisis and Hurricane Sandy while keeping my rental and generating monthly cash flow.

Been there, done that, and we don't drink so our nightlife would be a movie and dinner.I want pets (cats, maybe a pooch) that can be allowed to spend time outside when the weather is nice.  

Typically, a roof would not fall under this safe harbor, however if you are in an area that experiences extreme weather conditions, you may be able to make the case that you have to repair your roof or do a total re-roofing at least once every ten years. 

December and January seem impossible especially if there is snow on the ground and/or bad weather.