After college, I knew I wanted to pursue my law degree and I ended up back in CT because I missed my very large Italian family (also law school is f***ing expensive so financially it made a lot of sense).

Being that we both have individual assets to protect, an LLC would seem like a no-brainer, except for the fact that setting up an LLC would rule out conventional loan sources. 

If you openly are seeking a mentor and the individual you are meeting with knows this I would think that is enough to imply you need assistance and do not know the inns and outs of REI.

Factor that in as wellI'd like to think we're capable, but would hate to dive in and find out I'm wrong lol - You need to make highly calculated moves and be financially stable enough with 6 months of carrying costs for you personally as well as the home you're financing to flip/rent/etc. 

If the home hasn't foerclosed on yet then it's owned by an individual(s) or an entity.

Ideally if you provide paperwork for review, and your financial situation doesn't change much from now until the time you're ready to refinance, you *should* get an accurate answer as to how much you can qualify for. 

Ive also chosen at times not to purchase it, but Im also in a financial position to be able to take care of the costs involved with fixing a title problem.

They'll want to see your financial situation, but also look at you as a professional. 

Since they are individual units, I am not sure if they can be bundled into one loan of 5 (my guess is that one loan is more efficient than 5 individual loans), but not sure what the best loan type for this scenario would be.

Start working on your relationships with high net worth individuals.