This creates an initial negative equity position that consumes the initial cash flow, sometimes for many years.

Do I initiate a lot of the updates/questions?

So, we found a California based lender that we started working with, and got our initial approval with a few conditions (documents etc.) that they need, no big hurdles. 

I was feeling unhappy with my initial coach so I wrote to the administrator of the course and asked for a new instructor.

The initial online material is $97 and the 3-day certification is $1,495 (after $1,000 discount), all which will be reimbursed with first few deals. 

The initial poster was pretty nasty and making a lot of inferences.

Upon arrival I noticed the curb appeal and thought it was overdone (of course, I initially didn't say anything to the owner).

In the multi unit buildings I put on lease "Each tenant shares responsibility for removing snow and salting on both walkways and sidewalk infront of property" and I have them initial before we execute lease.

I've had a long career in community development and have a lot of bank contacts that would likely be interested in investing, but I'd need to prove the concept first with an initial fund (there are also a lot of other community development tools that could be leveraged to maximize and scale this).

It sounds like you have an un-permitted unit, which is essentially always a risk since there has been no notice to the AHJ that it exists and they can therefore initiate a code case to have it removed in most cases.