I know the potential state specific trigger if I transfer to my LLC in future, but difficult to obtain loans in an unproven LLC's name. that being said, do I insure the address under my name or the LLC listed on the STR business license?

When it comes to finding properties, AI tools like PropStream and DealMachine automate searches for investment opportunities based on specific criteria. 

So it does appear to be possible to get an FHA 203k loan for a 5-unit & convert to a 4-unit.When possible, aim for the Limited (aka Streamline) 203k loan, as it's less complex, not required to get an FHA consultant, etc.Of course, this is based of the two following important assumptions:1)  zoning allows for this2)  and obviously I owner occupy for at least 12 months3)  the total purchase price + renovations are within the FHA loan limits specific to my areaWhat I'm confused about is the timeline or chronological order of the process? 

DM me, and I’ll point you in the right direction based on your specific goals!

If your brother is looking to invest in real estate largely from a tax reduction standpoint they should pay a qualified real estate tax strategist to review their specific situation and what may or may not work for them. 

If you have specific questions about property management, I'll be happy to help! 

That way you get specific recommendations for your area of interest.

Does anyone have recommendations for good, reasonably priced countertop installers/fabricators who do work in the north/northwest suburbs of Chicago, specifically around Prospect Heights?

Any specific contract clauses or safeguards I should include?

That can be market specific.