Any guidance will be extremely helpful.

$100k in the bank is EXTREME overkill.

It will take an extremely well researched and laid out plan from initial purchase to the Refinancing.  

The process was hard, fun, challenging, exhausting, and I can't wait to do it again.Now we are going to take the next 6 months or so to save, educate ourselves, and network.

I would love to find a duplex but they aren't extremely common here, but I also would't mind a SFR to get my feet wet with the process.

The house were wanting to buy is a major fixer upper deal and is going to be completely as-is, And is extremely cheap (less than the assessment value on just the land) we may even just buy it with cash and finance it later to get the cash out.

It is free and the students are working under the supervision of licensed, and often extremely knowledgeable attorneys.

Additionally it's extremely hard for me to trust any property managers, brokers & real estate agents out around in Boston because they aren't familiar with their own laws and rent out places that aren't even habitable or to state code ( for brokers/real estate agents not their responsibility but seriously, that's just morally wrong). 

Extremely negative.

I have decided to take the course to get my license and I really go the extreme and take full advantage of time while still working full time job.