Doesn't seem to be a lot of options around here for that though3) Continuing to rent where we live, and buy a separate property to rent outI personally feel like having my brother to help out as a renter is a huge advantage.

You will be sued personally and everything in your personal name is unprotected.

Make sure your listing highlights proximity to the base, schools, and other conveniences.Lastly, a personal tip: When renting near a military base, be prepared for quick turnarounds.

This is a really personal question specific just to you.  

Quote from @Kenzer Hodgson: Quote from @Trent Reeve: personally, i think a dynamic pricing tool will pay for itself (should be around $20/month). it will help with far out/near time pricing, minimum stays, etc. 

If you do rent to this person, don't act shocked when they fall behind or don't pay at all.

Sometimes when placing an offer --  the POS is not yet available - and when you place an offer you can make your offer contingent upon approval of these items... although in order to have a competitive offer in this seller's market you are basically forced to "assume" the pos violations once they become available (usually 2-3 weeks after it's been ordered) -- you should be able to tell if anything more serious might come up on the POS via your own personal inspection. 

I thought any number of times of pulling those cards out of the deck, it's too unrealistic and too much luck for the person who draws it.

Plus, we revise the vision yearly at QB, our Chicago General Contracting Business, because it is constantly changing, and it's not my vision...It's the business's vision.You can do a business vision or a personal vision. 

Personally I think it's great as I was already doing this (I do not work for free) and now my competition has to as well.