That being said, if you can find an older property in a stable resort close in to Disney, and redecorate to a high standard, you have a great investment property on your hands.

A rental next to a university would be more stable than a vacation rental and more than likely when you to sell.more buyer for the rental over vacation rental.

Plan to retire at 55 for sure. 

The investment itself is not really worth it for me right now as I'm not even going to be getting more then how much I make in 1 1/2 years at retirement base on their calculations.

If you are nearing retirement, then the cashflow might be nice.

There are a few locations that we're looking at where the estimated rent value would be around double the mortgage payment in a stable economic area and we would like to be able to pick up some of these properties sooner rather than later.

We are focused on our retirement and our three young children’s futures.

Tenants that live like this have a tendency to allow maintenance to go unreported, which could cause severe structural damage that costs much more than the benefit of having stable tenancy.But in this particular case...he does report maintenance and there are no problems with the apartment despite 30 years of living like this. 

My Question is how should he go about taking the money out of his TSP, he is concerned that a withdrawal would add to the taxes he has to pay now, he could wait to withdraw till he retires in 5 years and is in a lesser tax bracket, because he will be earning about half of his current income once he is retired.What would you suggest the arrangement should be with someone bringing money to the deal?  

As we approach “retirement” from my day job in 15-20 years, we will begin paying off the older mortgages on the rentals.