It can be very rewarding and extremely profitable, just use the proper resources to avoid the pain. ;-)

Depending on the location of the property, the numbers seem extremely thin for what can easily be found in the area. 

Any guidance will be extremely helpful.

I'm a GC, not a structural engineer, but I can't think of any application in which a 30' span would be covered by a tiny 4x6 wood beam with no middle supports.

$100k in the bank is EXTREME overkill.

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

I wouldn't have to pay capital gains because I lived there.The main house has two separate apartments and a tiny house out back.

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.