@Basit Siddiqi gives you a good work sheet to figure out your true gain and tax.My thought is that simply selling and paying the tax because you want to move fast is short sighted. 

Do you plan to close are you simply trying to work as an unlicensed broker?

We're comfortable we've come up with a workable solution that fits these limits if we can just cut through some of the red tape and compete the project in under 12 months.I'm told the certification alone can take 6 months to a year.

I work at a community college assisting students that are new, on academic probation, foster youth, and/ or those who simply need resources and guidance.

However, all they could say was that they weren't cut out for it, that somehow I'm different than the average person.Maybe I am.

Just that the market combined with your state of mind tells me clean break.You can sell all as a package and 1031 into a passive investment and collect your 7% - 8% for the next 20 years but its too small for a big group without a  huge hair cut. 

Very simply... it's two different business models.

Last night one of them set up a circular saw and was cutting wood for their bonfire at 9:00 at night.  

If you get some deals done, a smaller company/attorney may cut you a deal if you keep bringing them work. 

I don't think this is cut and dry but i typically try and see what might need to be done to occupy it, how strong the market is and what do you have to do to get a deal done because you don't want to pass an opportunity for paying a little on the upside but also don't want to overpay on something that has some question marks on it as well ( plus this is work you have to do which it would be good to be compensated for )