Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with zero or negative relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560, little to no good tradelines, lots of collections & chargeoffs, recent evictions.

If so, they will automatically submit this for you to the proper agencies.I assume you're not talking about income tax or other taxes?

I think a full time income as you learn the business will allow you to sidestep some of those pitfalls. 

They are all on the same sports team and have no "proof of income."

Both meet the income requirement of 3x rent on their own and have excellent credit repayment histories.

Here is where the strategy comes in:When you move 401k stocks to a brokerage account via an NUA transaction, you pay income tax on the cost basis (And maybe a 10% penalty) but NOT on the gains until you sell. 

Then, weigh the options: sticking with the current rent ensures ongoing income but might risk tenant dissatisfaction, while offering a reduction can incentivize renewal and save on vacancy costs.

When I discussed the possibility of going into real estate with someone I trust, he said that I should not expect to start earning back my investment of time and money for 6-12 months.

Best case scenario this year between the 2 of them I break even with rental income. 

First thing you need to do is identify if you are wanting an income play or appreciation play.