Would there be any harm in taking an herb such as Licorice for an extended period of time as a male since it's antagonizing to Testosterone production?

No, just keep the dosage down. The best way to do this is by using it in a formulation, which can include the saw palmetto, pygeum, and jiaogulan. You can also use the licorice root topically as I mentioned earler.

I've often wondered this in regards to DHT, is it logical or even possible to attempt to use herbs such as tribulus to maintain elevated testosterone levels for exercise and weight lifting purposes while also trying to block DHT with another herb such as Saw Palmetto.

Yes. It is not the testosterone causing the problem, but rather the DHT. But high testosterone levels does not automatically mean high DHT levels. Sterols from food or herbs can block that conversion.

What I'm trying to figure out is if the DHT itself is the aspect of testosterone production which leads to its anabolic effects directly or is it only one fraction of overall testosterone production?

Testeosterone can convert in to DHT, and DHT plays a role in the anabolic effects of testosterone. So you want to control, but not eliminate its production. DHT has a mild anabolic action itself.

I'm currently using some tribulus powder as I find I feel better from using it & it's boosting my energy levels. However I've also been experiencing hair loss over the past year (due in my mind from adrenal burnout).

This is possible. Proper adrenal function is important for proper thyroid function. And low thyroid function can also lead to hair loss. But the hair loss will be from all over, not like male pattern baldness.

Can I have the best of both worlds with testosterone boosting & keep my hair? : )

A lot of men with high testosterone keep their hair. They keep in on the nightstand beside them when they sleep. Just kidding, it can be done.