(knock on wood)My question is should based on the current market does it make sense to flip this property and make a nice profit which I can then use to find an off market multifamily at some point or should I stay my course and work through the busy times get a tenant in there and collect the nice cash flow for years to come?

REI isn't about collecting properties...it's about collecting $$$$,....cash. 

Now if this month doesn’t work I won’t be nice again…Consider yourself VERY lucky… I use 3 attorneys regularly here and they all echoed the same sentiment… landlords here, including commercial property owners such as us, have absolutely no control over collecting rents… so much so that our clients are doing us a favor by paying.

If you want flexibility, I would not collect it to begin with just to be on the safe side. 

It all comes down to risk tolerance and your individual situation.It should go without saying, but insurance companies are profitable, which means in the long run they pay out less than they collect, which means that essentially you are paying them a lot of money, for only a little bit of repairs.The caveat of course is you need enough cash on hand to cover deductibles. 

I kept the house , been collecting rent since 1992 .  

Bad ones will be the ones that do not want to give their social.You are a landlord and collecting sensitive information is part of the job!

I was looking for some collective thought on my approach to get this property up to market rent.

Not fully managed, but includes rent collection, a call center/chatbot, and some management & scheduling of repairs & maintenance.

The taxes/fees that National Grid collects go partly to RISE so that's most likely who they referred you to.