I have the REIpro software..

Other than submetering, I'd recommend you ask to see the leases and whether each person has a security deposit that matches their present rent.

Because this deposit typically transfers over to the new tenant's security deposit, should I be charging an amount equal to the security deposit or only a fraction of that amount?

I do not like our current software Rent Manager.

Private owners are more generous with giving back security deposits, are less likely to raise rent, and free furniture is free furniture!

I have access to more capital, and I want to get away from my software sales career,  I'm passionate about my own business and I'm demotivated with the pressure of what I'm doing 7-5 (this is conservative, there are 65+ hour weeks that I'm being paid OT time on....)In a nutshell, I'm making more money in my 9+years of software sales. 

I would talk to a good securities attorney like @Jillian Sidoti to see what issue you may need to deal with. 

Whereas you would ordinarily indicate earnest money, down payment, financing and total purchase price... in an owner finance deal you would spell out the exact financing terms such as:Seller agrees to finance $x of the purchase price at y% interest over z years, secured by a first lien deed of trust.

You will likely even have to get a secured credit card to kick start your credit.

Who gets to keep the security deposit money under an eviction?