This includes cap ex, repairs (will a renter leave the property in the same condition you hand it off in?

On a related note, after leaving the military, my wife and I purchased a home in the Baltimore area.

If you can buy a home each time you move and leave a trail of rental properties behind you, you'll be FIRE before you know it.

Based on my 20+ years of real estate experience, I’d say renting the condo might not be the best option—$2,000/month rent minus $800 in condo fees leaves you with just $1,200 before taxes and maintenance, and seniors' condos can be tricky to rent.

Getting you to finish the work and then to leave are other problems I see in your "deal structure." 

If I were you and you need to meet the requirement of working under a Broker, just make sure your agreement with the broker allows you to take all your properties with you once you leave, obtain your brokers license and start your own brokerageI would also start looking at software systems and joining the National Association of Residential Property Managers.

It seemed that just having some kind of communication back to the resident right away was better than them leaving a voicemail.

This leaves $2600 after debt service (PITI).

This then will leave the property free and clear.

If a guest stays for one week in July, the owner can't legally rent to another guest until August and must leave their unit vacant for three weeks.