Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

. -- Unincorporated counties -- historically, the more conservative, skeptical-of-regulation type of government bodies -- have clamped down.

Hope all that makes sense. 2) LLC-B contributes $5875 towards retirement --> tax deduction what type of contribution is this?

Next question.... will you self-manage it, or turn it over to a professional management company, or some type of hybrid? 

Types of current tenants. 

Have you decided what type of investor you would like to be?

I'll settle for a variation of this and give a little, but I simply pass on PMs who hand me a term sheet with 10+ different types of fees.

are we talking Idaho Montana CA  NV type of remote ?

Another option is investing in real estate through partnerships or fractional ownership, focusing on properties that yield cash flow or appreciation potential.For long-term growth, consider diversifying into assets such as private equity, tax liens, or even certain types of real estate that offer both capital appreciation and income potential over time.

Meaning how to attract the type of people you want to your STR listings and how the heck you are supposed to know if there is a market for your type of "customer" in the area you are investing.