It has come to my realization as I put up all of the money I have worked so hard for, that he has no skin in the game.

If the numbers work for you and your investment goals, it is always a great time to buy.You never know what tomorrow holds, so make your decision based on the information you have today.

The holding costs on a GUC project are likely going to run 9-12 months or more depending on the municipality.

The properties you are selling and buying in a 1031 must be properties you intent to hold for investment use. 

Escrow is a neutral party that holds funds so opening escrow as soon as the contract is signed is normal and sometimes done before a property is under contract.

If you have the capital you're alluding to, around $150K, there's better routes to take than SFH BRRRR and depends on hold periods.

If you're just going to hold a couple of properties, the cost benefit analysis may not pan out, and you will definitely get sued personally if your LLC gets sued.

Is the back end of the financing always such a drastic risk or is this typically someone looking to cash out quick and leave someone else holding the bag? 

It sounds like my own bias is holding me back. 

I actually managed to get a quote for a conventional loan recently, just so happens that the only thing holding me back at this point was my job.