The unit traded 2x subsequent to my disposition, both times for less than my sales price.

@Joey Chrisman From what I think I know, if you do the work yourself (no subs or specialized trades) on your own property, no GC license is required. 

As there hasn't been any, we have to take the IRC and Regs at face value.In a nutshell, it's a trade or business determination.I imagine if you sell a rental property at a substantial loss you're going to want to take a 1231 loss (trade or business) instead of a capital loss (investment)?

If you take out a loan from the cash value account it affects how long your policy last so if you were sold the policy with the notion that you can take out money later without consequences, it's not that simple.

Should I attend a trade school?

There are many that wish to sell and trade up right now but they don't dare do it because they'd be homeless if they sold right now so we just have to wait it out.All of that means 2 very important things for investors - Appreciation is fantastic and rents/sales prices are climbing so your returns in this area are guaranteed to produce!  

It is good to hear from someone in the trades here as well as it doesn't seem like enough of them are represented on this site.

So I’m selling two seasoned rentals and aim to trade them for 4 units.

Then when you have enough equity in that same DST trade up for a bigger multi family??

You could sell and trade up, but I would prefer to refinance and buy more.