I'm just here to note that an LLC does not offer a single tax benefit, nor does it allow any deductions that aren't allowed without an LLC. 

If borrowing, use a non-recourse loan since personal guarantees aren't allowed.

Electric: is the easiest to split, but may require holes cut in walls to separate the units.Gas: gas lines aren't as flexible as wires, but it can usually be done affordably.Water: most cities will NOT install additional water meters on a property.

We currently own/manage properties across a few states including Hawaii so we aren't new to managing short term/mid term rentals.

Tax Savings:While it’s true that the stock market has been strong, real estate offers unique tax advantages that aren’t available with other asset classes.

It still shocks me how many agents aren't aware of things like the fair notice ordinance.  

I'm not familiar with these platforms, but it sounds like they aren't mature enough yet to capture the important nuances that Chris mentioned.

If you aren't familiar with Baltimore, I would suggest it's a hard no and say that you are trying too hard to make cash flow happen talking Baltimore and tax liens and auctions.

Tax-Free Exchanges: While 1031 exchanges aren't available to SDIRAs, the tax deferral within the account means you can sell property and reinvest proceeds into new opportunities without immediate tax consequences.

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?).