Linda,Do you avoid triggering the due on sale clause when stating "deed prep only, no title exam conducted" on the face of the deed? 

You can do it creatively, some upfront + payments + back end, with triggers for everything.

A lendor might be talked into something but in general the change of title triggers mortgage releases etc and is a non-starter.  

I've been learning as much as I can over the last few months so I can finally pull the trigger on my first property with confidence.

I'm not quite ready to pull the trigger on investing just yet, but my primary residence is in Middlesex, and my husband and I are considering holding the property and renting it when we move on to something else in the next few years (we got an awesome deal when the market was still bottomed out and now have over $100k in equity when we only paid $200k for it).  

First, make sure a transfer to the LLC  wouldn't qualify as sale to the lender (it might trigger a due on sale clause.)

Keep the irons in the fire on both ends, that way you aren't coming out of left field when its time to pull the trigger.  

Obviously this is a very big decision for me and I just want to get all my ducks in a row making pulling the trigger.

Should I pull the trigger and buy it, or wait for a better deal down the road?

The building permit may trigger the reassessment automagically, but you should ask the city specifically.