I have an eerily similar dilemma and background. When did you hear back from Wentworth? 

After $$ and location preferences, I suppose we should be considering ideal employment opportunities - do you want to be doing more design oriented work or focus more on construction/materials?  WIT seems to be pretty well respected in Boston, but maybe the name doesn't go as far nationally? Depending on type of firm though.

I'm just speculating, and would also like to hear from people who have been through it. 

Have you visited either school?

I found out about Wentworth just the other day.

The plan is to be licensed and to work from design through construction. I'd like furthering my education to support becoming competent at both. I have no interest drawing things up and pushing them on to the next guy. As well, overseeing the sourcing, fabrication & installation of a project when you had no or little role in the design has it's drawbacks.

I'd rather go to the better school or at least the more well known school (Pratt) if I feel this can get me where I want to go in this respect but Wentworth seems fine from my research and If it suits my interests/strengths better, then I might get more out of it.

the owner of a pretty high end but small architecture firm I'm working on a project for at the moment in NJ says that he's hired many people from WIT. So WIT's name at least seems spread down the east coast a bit and a job at this guys firm (or similar) would be great.

I haven't visited either but I grew up in NJ right outside of New York City and I have family in Boston so I know both area's well enough to know I'd be fine leaving in either. 

Sounds like you're self aware and goal oriented enough that you'll be fine either way, but still a tough decision since it seems the experiences will be pretty different. 

Would love to hear what you decide on and what insights push you one way or the other. 

Caveat: I don't know much about WIT 

However, there's a lot more opportunity in NYC than Boston and going to Pratt will help you navigate that world better (faculty connections, firm meet n greets, etc). It is heavy on the comp design, but I think that could be a bonus for you coming from a heavy 'practical' background. Also, it is not uncommon to take Construction Management classes your 5/6th semester, so perhaps that's something that could benefit you.

As others have mentioned, you seem to have a good head about you, so you'll probably be fine either way. 

I went to WIT (BS-Arch & M.Arch1) and am registered. 

I'd recommend going where you have less debt and in the metro area you want to work. Networks matter. Being in debt severely limited the risks I could take and places I could work. NYC/CT I'd say Pratt.

Either should prepare you fine. I'm pragmatic and technically oriented. I enjoyed WIT and as a new grad knew how to put together a buildable drawing set better than my GSD co-workers. They were more creative. It sounds like you're already experienced, so maybe Pratt would be better.