I wish you well in your real estate endeavors. 

Yes, they are actually selling individual units as well

And yes, the income from renting is still taxable, but ideally you are offsetting a chunk of that with depreciation which is a non-cash expense.You should read Amanda Han and Matt MacFarland's books as well which are available in the BP Bookstore. https://store.biggerpockets.com/products/tax-strategies-book...

The alternative to that is going to the Cape, Western MA, as well as adjacent states with coastal/lakeside properties where many of us New Englanders vacation. 

I will only get one chance to set my real estate foundation, want to make sure I do it as well as possible without suffering paralysis. 

There are a lot of positive ROI options in that bucket.To answer your question anything on the beach will rent well. 

So I would like to get these things hashed out well beforehand as something to present to potential clients and have procedures for my company.

I highly recommend a well-qualified REALTOR who works with investors and knows how to help you best.7.

I called my local insurance company, as well as two major companies and was told "good luck." 

,Well, I'm not sorry.