I presume your system will be to receive call and manually qualify and convert.You've got the rest of your life to test and tweak your system.

I certainly want to ensure that John is still incentivized but I also want to make sure not to pay 'too much' as he's getting two commissions for presumably less work/time than two seperate deals.Thanks in advance

On the other hand, you could presume that motivation to sell increases with time.

However, that presumes that there is some cumulative effect that your mail pieces have on the Homeowner.

Presuming it is true why doesn't your broker tell the complaining agents to pound sand? 

If they don't get redeemed, they can take the property, which presumably they've researched and determined that it is worth more than the total amount they paid in.  

You are "presumably" in this to make money.

With the income levels you described and presumably the housing assistance from the military, you would benefit from buying over renting.

This sets you in a class above as you actually have some dough and presumably, some experience. 

If you have the cash to invest on the second property, it would be a good idea to do so out of state since I presume you cannot house-hack again until next year.