I feel like if it is done correctly (and trees aren't denting it) its a set and forget it. 50 year life expectancy on metal and asphalt shingles will be 1/3 of that. 30 yr only last 25 and 15 if you maintain the shingles. 100% Metal and the insurance company should cover all of that. 

I've been working for a company that is in the process of doing this.

@Austin JamesUnderstand the area, the current tenant base,the median income, is it in a flood zone, the age of the asset, the condition of the plumbing, the electrical wiring, the fuseboxes, the age of the roofs, the age of the mechanicals, the condition of the foundation, the drainage of the property, does the property have a C of O, is there ny environmental concerns such as oil tanks being buried, the current property management company, what are the amenities.These are just a few things to look out for.

This time I called Rtr and they said, "we need to switch PM companies to "PM company B", we have had a lot of complaints and have been moving a lot of Rtr customers over to this new PM company for a few months.

Yes you will find an agent that will continue to write contracts for you, but you have to ask yourself and you really getting great service?  

I am not a STR specialist in southern Maine, but I can connect you with a management company that is and would be able to give a more exact guess.

You also have to remember that these are most likely (am assuming here) paid off properties - it's unlikely a mortgage company is going to let the taxes go unpaid.

Hi @Dave Allen I have all of my rentals in separate land trusts and the beneficiary of the land trust is my LLC.I use a local trust company to be my trustee and have another great resource here in Orlando as well.

I lived in one side for a year then moved and now both sides are rented out with a property management company. 

I would probably continue to work part-time hours for a few years after that... but would be happy to stop if I want to.