I also know that in many cases the llc will protect my personal assets and I fully believe this is either analysis paralysis or just fear of failure. 

As that will at least help folks that you reach out to know that you are a real person, with a picture and professional bio.

It sounds like the title will be transferred to a land trust, and my LLC or I personally will be the land trust beneficiary.

I am by no means an attorney and to my limited knowledge I don't know of anyone who has gotten "caught" with the new illinois law, but my understanding is that you can not "Market" (aka sell side of wholesale) more than one property per year.So if you had a licensed agent do the "marketing" of the property once it's under contract then you should be in the clear.You can of course double close, but the law is more specific to the marketing of the property vs. how it's closed.My suggestion @Andrii Sazhnev would be to find another wholesaler who has their broker's license to work with them while starting to get your license...in my opinion (if you have the time) it is worth it for anyone who is doing real estate full time to get there license - simply for the education and MLS access.

I’m aware of what material participation is, i just wanted to see if anyone has personally done this and if there were any issues or pitfalls with doing it.buy a million dollar cabin, cost segregation, 200- 250k tax deduction against w-2 income and rinse and repeat?

They can walk in to a local branch with cash or personal check, or pay via ACH bank transfer online. 

Which means I may well have been the only person foolish enough to bid on it, among the billions of people with internet access.On the other hand, the fact that the owner didn't pay taxes since 2018 is not a big red flag.

I'm thinking I may need to seal/coat the exterior walls - one person I talked to thinks moisture may be coming in from the walls and getting sucked into the soft bricks.

I've done this with my properties because I'm well known in my small town and don't want people to know what I own.LEGAL PROTECTION: By placing your assets in an LLC, you are legally separating them from your personal assets.

I am a board member with CFRI, the local chapter for the national REIA and I personally know about a dozen private lenders that are members.