Can I charge him my late charge which is currently $100 after I get the rent on the 19th? 

But upon looking at court records this person has multiple driving violations and charges of criminal trespassing.

You get to rent to professionals who are less likely to trash your property, you get to charge a higher rent than long term, and you're being paid by large, 3rd party companies that are extremely unlikely to not pay rent.

I would 200% be doing this if my current partner wasn’t so averse to moving frequently.

A good CPA will provide greater value in advisory and tax savings through proactive tax planning than the fees they charge.

Tenant PotentialRental Market: Study local rent prices to understand what you can charge.

I pay all the subs directly so there is no up charge to me.. and I make sure everyone is paid so their are no liens.on the 90 lot development i am 3.4 through..

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.

How much was the HML charging in interest?

Quote from @Victoria Phifer: I don't recommend charging anything on a credit card unless you have total control of your finances and can pay off the balance every month.I charge everything I can to credit cards, but I pay the balance off every month, 100% without fail.