My main concern is that I don't have any construction background and I have never rehabbed a property before so I don't have any real world experience regarding the costs associated in doing so.Once I find a deal that looks promising on paper and I physically go walk the property with my realtor how am I supposed to determine a rehab estimate without any prior experience? 

You won't know until you physically check on your property. 

That requires a physical presence.

With town homes, you own the physical structure and the land upon which it sits.

It's pretty resilient, and hangs on, but it's up and down.I know it looks great from Boston,  (it's only 2.5 to 3 hours north) but it might as well be on another planet in every way. 

this was physically painful to read.but congrats on the sale/deal!

As of now, there is a 1400 permit "freeze" which expires next year, but could well be extended. 

I know it is illegal to discriminate, but has anyone purposely created a STR for physically handicapped vacationers?

It comes down to the format of how the address is written; I once had someone ask if the mailing address I provided was my physical address.

This is not worth your time, money, & emotional well-being!