You probably won’t be able to sell with 9 years without taking a loss.

There are too many people selling you on how easy, passive, and lucrative real estate investing is.I always tell people the first year or two will be bumpy.

We're looking to transfer this into an LLC for liability purposes.From what I can tell, the best way to do this is to retitle the property, pay Chicago's expensive retitling tax, and set up an operating agreement, all of which likely requires a real estate lawyer (what $ base do we use on the tax, given we aren't selling it to ourselves, just transferring it?). 

If I do move in the next few years because of the military, I will decide if I want to sell for the appreciation depending on the market. 

Let us know when it sells.

From a personal standpoint I target 70% LTV for any investment I have that way gives me ability to sell it if I need too

They can sell tax free.

It would be wise to rectify it before transfer of title so your starting off clean and hopefully won't have any issues when you go to sell down the road. 

If you are considering buying using Subject To - Subto, it's important to know what your exit strategy is.Talk to a mortgage broker (not a bank) and ask if that is a property you will be able to get financing on in the event you have to refinance quickly, because the Due On Sale clause was called.AndTalk to a real estate agent about how much you would have to bring to closing in the event you had to sell quickly.

I see agents and wholesalers trying to sell properties that are supposedly wholesale, but they sell at retail after it's marked up so much.