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. 

I think partially because a lot of folks don’t even check it.If you’re interested in getting more off market deals I would suggest starting relationships with brokers that sell the types of properties you’re interested in.

Anyone trying to tell you a certain asset class is good or bad these days is probably trying to sell you something.

Keep in mind that I am selling them as affordable fixer uppers and usually only address any health, safety, and functionality issues.

We don’t sell property, but I can recommend the two gentlemen who replied to your post, as they know the STR 34747 zip code well. 

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?). 

Selling and buying something else you want keep and doing a cost seg in would help with the tax burden probably better in this situation.

There are others there selling. 

Anyone want to sell me their contract from this course?

In your example, they bid the property to $225k because it's worth $300k so they're going to get all their money back when they sell it.