I would suggest in speaking with banks about the option of refinancing either of these homes separately or together.

I managed the properties myself, and was offered a job out of state that required long-term international travel. 

Him & his team started and finished the job in one day.

Most of what you suggested would be an arms length transaction and wouldn’t pass underwriting anyways and cost time and money to do the deed transfers and such! 

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.

Also since you are new, I suggest you do not go down this path, All the best 

The software they use is really nice and easy to use. and they do a great thorough job, providing many of the typical inspections themselves (Whole Home, sewer, Termite, etc)

You can suggest to set aside money for CapEx items but they get capitalized in the value of the home i.e.

I would also suggest you reach out to someone who has experience in the BRRR method of investing.

He's still able to commute to his job in DC (the drive is actually a bit shorter now!)