I remember paying Nicor (the natural gas company) some months over $300 just to heat the house.

The Property Code presumes that 7 days is a reasonable period of time for the Landlord to repair a condition unless there are circumstances which establish that a different period of time is appropriate (such as the severity and nature of the condition and the availability of materials, labor, and utilities.)Tenants have more rights now than they ever have had in the past and Judges are normally on the side of the tenants.

But I would like to hear from seasoned veterans who have perhaps dozens if not tens of dozens of flips going at once; what is the natural progression of house flipping once you move past the mom and pop stage?

You do not have to file a new company which the two of you join either as natural persons or as companies.  

Due to the nature of the military life, my wife starts at the bottom every time we move (not conducive to growing her salary, but adding to savings none the less). 

I am 19 years old, am currently working as supplemental IT and do rapid prototyping for a machine shop, in addition to attending Purdue's New Albany branch for mechanical engineering.

We have natural gas in many of our units.

The buyers are more well capitalized, the sellers are more professional in nature, and the property has a professional management company keeping books in a way that a lender expects them to be for review.As a broker you do not get paid until it closes and your investor doesn't make any money as well looking at dud properties that never work out.Everyone wants to succeed and make great money.

Once you have determined what approach works for you, additional information can be supplemented through reading and asking questions on the forum (as you have done.) 

In light of the nature if the issues, you should be able to convince the current custodian to release your account without any termination fees, since they clearly are incapable.