My question at this point is two fold.

Not quite sure of your question here as it appears two-fold. 

These lessons applied to your next investments will pay you back many fold.

I've got a physical office but there is just folding table and a chair in it.  

Love them or leave them, because people have had mixed reviews about some of the educational avenues we have invested in but we are pleased and it has paid off 10-fold.  

PS Bonus points for ability to generate 3-day notices from the software, and ability to dispatch physical letters without manually print/fold/stuff/stamp/mail  (ala mailaletter, click2mail)

My thought is while that sounds great on paper, if we end up not finishing on budget and the contractor now has 20k of our budget (hypothetical number) in his pocket, and we end up bankrupting and closing the door on this venture, there would likely be bad blood about him having profited well while our business folds up.I see a strategy where his expertise is leveraged to oversee that bids are in the right ball park and work is being done properly as well as compliance type issues (permits and such) are all in order.

We then stamps and labelled each envelope, folded each letter, then stuffed and sealed them all.

Assuming you are successful that success will be magnified 10 fold based on their initial negative response.

This is my first time posting in a long while, but glad to be back in the fold.