There ARE people able to create enough hype, misdirection, and lies to successfully conduct a “Capital raise” without possessing the experience, education, knowledge and analytical ability necessary to have a fair shot at success.  

Definitely best exterior front shot first.

This will provide consistency and clarity in how you handle your properties.Start by reviewing your current Property Management (PM) agreement.

So we shopped it out to our consistent buyers but at a strong price of $75k.

In the case of a successful tort against you, you might regret commingling funds in a single bank account, but I can't see how keeping them consistently separated would ever burn you, even if it is a bit less convenient.  

If we're consistently profitable and find that the cleaner is not effective in responding to guest needs, then we will not hesitate to go the dedicated on-island agent route.

It is my understanding that the company works out the tenant billing rates based on your master utility bill to keep it consistent and fair.So, the technology exists BUT is it legal in Maine to bill the tenants in this way?

Biggest thing IMO is getting close to the train station and have a high quality units that may not look attractive on paper the first few years but will have the ability to raise rents consistently long term. 

While it doesn't meet the 1% rule it's in a stable, desirable area that'll perform more consistently for you over time so it's worth the tradeoff in my opinion.

For many owners, this is a win.Other owners may value the consistent monthly deposits rather than worrying about the usually seasonal STR incomes.