We are planning to start flipping and transition over to long term rentals in 3-5 years. 

No car.. don't bother.. unless you become a commercial agent that works in a certain sector with a large firm in a large urban area where you can manage walking or taking efficient public transit.. 

Great planes I bought mine new in 04  that was cool going to Duluth transition training and walking into the hanger seeing that brand new bird :)I have about 1000 hours in it.. not as much as I like.. and right now I am battling my medical.. so been grounded for while.Anyway safe flying.. and I really really enjoy working in Charleston SC  great people great place.. !!!!

Transitioning from one business to another isn’t a tough decision to make if your reason is your family.

At this point, I'm working on getting into my own investment properties in order to transition out of my current management role. 

It's hard to stand out.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

Having them around will help me transition into being a landlord with as few headaches as possible.

He will be shortly leaving a high pay stable job (military pilot) for a low paying (40k/yr) job and it looks like this transition might be preventing him from qualifying for a cash out refi.

I've been interested in real estate investing for several years, but didn't want to take the leap until life had settled down a bit (getting married, transitioning out of the Marine Corps, etc).

You may also want to consider other places that have mass transit planned.