The money partner leaves $10,000 in the account for any incidentals and we split the profits or the losses 50/50 until we sell in within the next 3 years.

I am looking into the possibility of selling it through subto. 

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.

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

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. 

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

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.

Even to sell the house, the house would need a new roof so that the buyer doesn't have insurance 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?).