Most S8 tenants have a history of bad decisions and from all that, many have only learned how to game the system.We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher and pretend to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

I don't see that you lost any money in the deal so I would just start over and not waste mental energy on the colossal errors of this former agent and team.

Student debt usually come with a low interest rate, a rate you should should be able to beat with even a decent investment thereby making it more worthwhile to invest and just pay the minimum on your student loans.Of course, there's also a mental aspect to this.

It took us 3 months to remove an illegal mentally disturbed tenant from an apartment who was sub-letting from one of the tenants. 

Don't waste any mental energy thinking about what the Fed does.Find good deals. 

The following is our approach, not just financial, but mental also getting ready for retirement.1.  

I don't know how much mental capacity I would have to handle it without it affecting my schooling. 

Currently, I don't have any second mortgages or helocs because the idea of keeping track of more than one mortgage per property has been a tad daunting and decreasing my cash flow at the moment is something I'm battling mentally with.

They have a learn as you go mentality as far as training goes so I feel you need to be a bit more self-motivated starting out as opposed to if you worked for a more well-known brokerage with a more formal training program. 

Kudos to you for trying to work through the current issue, but the S8 "entitlement mentality" is unlikely to get easier to deal with.