I read the answers here and don't see anything problematic if we simply transfer the lot to the new LLC, and sla as the Trust is the only owner of the LLC.

Deciding what strategy to go with for your first investment can feel like a lot to handle.

Hello there @Jane Mun - There is a lot to unpack there my first suggestion would be to connect with @Samuel Pavlovcik or @Prashanth Mahakali who are also both Chicago architects.  

This is very helpful and gives me a lot to look into! 

There is a lot to learn to ensure you don't get ripped off (and even then there is a risk).

However, we still had a lot to learn in order to be successful in the space. 

Travel to conference cost me $5k per week so always assumed id need a lot to purchase abroad and own for minimum of 5 years.

there just isnt a whole lot of things in that area that scream the need of a STR. not saying you cant get renters, there just isnt a lot to attract them. 

I will say that i get very anxious when I read folks recommending folks put their hard earned down payments in lower quality areas with low cash flow and equally low appreciation where the investor is far away and has zero control over their investment  it makes zero sense to me   I have a lot to learn still but I always analyze my assets and try to make the wisest choice and sometimes that choice is doing nothing..

Rate of expansion has a lot to do with personal risk tolerance.