It will familiarize you with the basic terminology and benefits.

The deal was contingent upon 60 day due diligence and a clean Phase 1 environmental assessment.

Do you guys see the benefit outperform the 2~3k price difference? 

And I feel the ideal portfolio can benefit from the diversification of both.I feel directly owned properties are great because they give me maximum control and the ability to tweak them exactly how I want.

Of course to maximize your tax benefit it needs to be sustainable over time. 

This will provide you two benefits:1) Help you better define the position, so you can hire a better matched person2) Make training the next person easier

What are the limitations and benefits?

Hiring unlicensed and uninsured contractors is considered  an exclusion under most property insurance policies, meaning you could be giving up that benefit as well.

It has almost zero benefit to have it to just represent yourself. 

Realistically, there should be no benefit, and there are probably some disadvantages, of doing what you propose.