I only plan to manage these two from out of state until we're able to refinance our second home as we're losing money on this particular house for rent as we bought this home last year. 

My tenants just notified me that their unit got broken into and money was stolen.

Mistakes I see people make is they plan on living there a short time and over renovate the property where they will never get the money they put into it back. 

And even a good PM will not watch your money like you do.

You have to earn a mentor by showing up a lot and then your mentor will appear.

Wouldn't it make more sense to raise money privately?

This would be a waste of everyone's time and money.

Yes you will save some money by self managing but more important you will learn what it takes to manage a property. 

I would focus on saving enough money that if I had a deal go bad, then that money I saved was there to cover it. 

In my opinion, if you pay a "kicker" to the seller, you're just taking money out of your own pocket and transferring it to a party that is not taking an equity risk in the deal.