You will discover more viable opportunities by being a good listener within earshot of the legal,professionals who encounter these issues rather than a guy who wants to get something. 

An LLC is useful for two things: anonymity and legal protection.

Stand behind the website company.

Is there any company’s that you can suggest that you have had good experiences with and trust or maybe another strategy of managing a long distance STR.

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.

I'm planning to purchase the SFR with a conventional mortgage, but my mortgage broker and underwriter are telling me this will create a lot of issues both legally and with the bank once I demolish the property and try to subdivide; since the mortgage is for the full property. 

There is a very big difference from a legal perspective.

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.