After falling for those for years, I am now a bit skeptical when I hear those "too good to be true" tales. 

They will fall under long term rental laws past 30 days in MA. 

My plan is to save up my annual income by mid-Fall so I can quit my job. 

What's the best option with low DP then the traditional 20%.. lastly of you have a awesome lender who is creative and can make it happen, please share contact Info. thanks  Sharing this article I published last year here on BiggerPockets on this exact topic - things are generally the same as when this was written up last Fall - your best bet is likely STR-friendly STR Lenders - ones that will use forward-thinking methodologies like AirDNA, etc. - probably about one third of DSCR lenders are STR friendly at this point (most will not do STR or have very conservative UW)Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

We are considering asking them to move out for a couple of months at the end of their lease so that we can rehab the unit, then have them move back in this fall once we are finished.How far in advance of the end of their lease do we need to let them know this? 

Also as an LO you typically fall under the licensing of the lender itself

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Folks could fall off and injure themselves etc. 

(Obviously deals fall thru all the time but knowing a property NEEDS to refi this year is what I’m getting at).

Quote from @Greg Elkins: I address this in my book in detail, but it won't be out until this fall.