Could be a mentorship, internship, or any kind of work that would allow me to get some real-world hands-on experience, but the problem is, I just don't know where I should be looking.

Month-to-month is only allowed with a 25% increase to the advertised rent.

I agree with the advice to use property management software from the start, as it will allow you to grow your portfolio more seamlessly.

Yes I have checked the HOA rules and they will allow a minimum of 6 months.

This would allow you to keep that low 1st position rate. 

Off-market deals can sometimes offer unique opportunities and less competition, allowing you to potentially find properties at better prices or with favorable terms.On the other hand, for the Dayton and Cleveland areas, you may find that there are great deals available primarily through on-market channels. 

I was looking for something that would allow me to take a picture of a receipt and categorize it in the right bucket under the right property.

Other things in his LOI were that we grant another option, that we refund the security deposit, that we allow unlimited assignment without us granting consent, etc..I'll go with your option #1 above and simply decline his other proposed changes and see if we can preserve the Renewal concept at a new rate that bakes in his commission (and then some) - if he wants to earn that commission, let him go and sell the package to the tenant.  

She also likes it a lot at tax time when those deductions come around.

If they have other property (outside of a primary residence) then it could work out but you have zero equity protection and going in 2nd behind hard money provides all sorts of risks and issues, even if they allowed you to.