And starting to get some money is better than no money right ? 

Now I've got a property under contract:$78K purchase$35K in development of utilities.$24K in soft costs (permits impact fees etc)$200K (or less) buildout of the house (size tbd on after-build-appraisal) Likely going with 2/2 A frame 1000 sf.

That is probably a good start to setting the goals you need to achieve to make the dream happen.

This has been a reoccurring situation over and over again and it’s getting me frustrated and I’m starting to question what exactly am I doing wrong.Thanks in advance.

I have been a podcast listener since 2011, only started posting here recently and its been a very supportive space.

The current owner bought it for $30K and I know they had to clean up a lot of title work and started doing repairs. 

At least in my area, it's cheaper to own a condo with the HOA dues than it is to pay for all the utilities, snow removal, waste management, maintenance, etc, that goes along with an SFR.

Congrats on getting started.

5) If approved, how much will they want upfront, when can they start and what's their expected completion date?

I'd start with Darien and Elkhorn first.