This gave us peace of mind and ensured that any unexpected incidents wouldn't result in major financial setbacks.These two choices have played a crucial role in optimizing our STR strategy, balancing profitability and protection.

If you understand the math of it all it should come very clear, the game is NOT best played (1) buying in all cash, (2) buying and sitting on a property for decades on end. 

It seemed like a long-term play with less price or industry volatility.

Generally speaking, Boston proper is an appreciation market (low cap rates) unless you have a solid value-add play.

and others that i did not care for their business practice .. but if i wanted to enter the pay to play business I think it would be worth the 20k a year to network with those dudes.. but not my bag 

Yes we tried everything, and Yes I know now that wasn't the best play haha. 

Umbrella insurance will never come into play for Property damage (fires, storms, floods, etc.)It is liability coverage only.I'm an insurance agent and have seen umbrella claims from fatal car and boat accidents. 

He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

If you're asking for my option and you want to play it safe, budget for 10% vacancy.

On most any day you could find people walking dogs, or children playing in the area.