I'm also pondering a pivot to STR, since small-ball investors like us are being put in the same "evil landlord" camp as the BlackRocks of the world...

I have a decent amount of money to help get this ball rolling, and time.

Tax sales are a whole other ball of wax, different than retail properties.

Allow me to polish my crystal ball and see what she says: Change.Yes change is always a constant in Real Estate.When more people feel comfortable selling and put their property for sale the skyrocketing values will level off.There is no hope of building our way out of this fast.There still are almost five million houses in forbearance, haven't paid since 3/2020- will those people find pre pandemic paying jobs?

No one has a crystal ball, but history and present day events are pointing more towards a down turn in my opinion.

I am closing on a full side by side 2/2 duplex near White Rock Lake and would like to start getting the ball rolling with a trusted, honest contractor.

I was hoping someone could give me a ball park range for these common rehab items for Boston so I can quickly calculate rehab cost. 

That will get you in the ball park for a long-term capital gain.  

Investors have a tendency to want to look at every property and then have you write a low-ball offer. 1) Find out if the buyer is truly qualified to buy, get his pre-approval letter on deck.

We actually put a few low ball offers in on neighboring properties, two of which were major fixers.