What area they seeing in your sub-market for progress, other properties being renovated, jobs, new business, etc? 

My guess is that the type of hands off 'don't want to deal with it' buyer you are looking for is also unlikely to be able to see past the 'ugly' current state of the house.I could imagine it working if you show them something finished (model home) and not show them the current ugly state.I heard a story from a high end ($50k tables) furniture designer who once made the mistake of showing the client the table in progress with clamps, glue and unfinished surfaces etc.

Did you ever make any progress in gaining any of this information?  

I think the insurance needs will depend on the overall strategy you are going to put into play and will change as the strategy progresses.

You have aggressively dropped down your student debt, I say continue the progress and pay it off for you can potentially buy a bigger home (4 fam) owner occupied once you are done.Or if you are comfortable with debt you can make a bigger return investing and that can help you pay down your debt. if you are I will get a owner occupied 2-4 family with a seller concession (depending how competitive your area is) for you won't have a high closing cost.

As you can see I'm really really focused on my future, I'm just at a standstill in life selling cars everyday and I feel as if I'm not progressing.

I’m still pursuing other leads as well but wanted to give an update on some positive progress!

I am able to consistently pay down the HELOC using my personal paychecks and some early rental income, and I am making progress, though there is a good balance currently.I'm thinking about changing these all to fixed 30 year mortgages.

Congrats on your progress thus far.

For me personally, I am wondering about how to benchmark progress.