Then I start asking around for how others have handled getting this last piece in place [maybe a first piece for others]... and finally I take a deep breath and put on my "I CAN DO ANYTHING" hat [it gives me confidence, lol] and call up one of my friends with lots of money.Background:  I thought I couldn't go to any of my "rich" friends until I had at least one deal under my belt.  

How confident are you that it will fly off the shelf at $290k?

Agree with Michael S. that knowledge is power and it will help to build your confidence the more you read and absorb the material on this site.Check out all the podcasts, I listen to them in my car during my daily commute.  

All this because the buyer can't be bothered to get it onto our state approved forms in which all other parties are more confident for their protections.I don't think you're doing yourself any favors trying to buck the system, particularly with so little experience.  

Once you get a few good ones on your team, it's awesome, because you are way more confident in making offers when you KNOW you have a buyer."

I would ask myself how confident you are that you can and will rent the other units out.

The earnest money should go into escrow rather than being paid directly to the seller.  2% is likely a sign that the seller is less than confident in your ability to close.  

What does the turnkey do that allows you to place that confidence in them?

This metric is used in Game Theory, market analysis, etc and I use it to make everyday decisions if I have confidence in the numbers.In this example, the probability of getting a  1 million if I choose the green button is 1 ( or 100%). 

You will feel allot more confident about using architects and paying them once you see how your project is moving along and see for yourself all the issues that can present themselves when paying to have so much work done.