While I am sure it is a great area for cash flows, flips/price inefficiencies capturing, the area appears rather stagnant in terms of long-term price appreciation trend.

It is completely legal--as long as you're compliant with applicable laws, including securities laws ;) In terms of how to be compliant, it depends on what you're doing, how you want to market, and who you want to take on as an investor.

How does the timeline look like in terms of lien data and mortgage date?

In terms of finding what you're looking for-it largely depends on the area.

Additionally, you can ask them about their specific experience with their syndicator, in terms of transparency, past performance, etc.Lastly, I’d highly recommend that you listen to your gut.

Or in terms of blackjack are you doubling down on an 11 or are you hitting on a 19?  

( In terms of rate, interest only and no prepayment penalty).What would the process be like working with a bank to get this?

Jenna, First off Worcester has lots of weird rules in terms of zoning. 

We are new to this area and would greatly appreciate any recommendations to real estate experts in the area in terms of investment properties.  

Yes, you should definitely hire an investor/agent, they'll speak your language and can empathize with you.I run the investment numbers on properties before I suggest them to my clients so that I know whether they're a good deal or not or what is needed to make them a good deal in terms of negotiations...which IS within my purview as an agent.But don't expect your agent to advise you on investment matters unless of course, they're also licensed, financial advisors!