Consider your budget, savings plan, credit profile, and financing options.

Or is it a community specific thing?

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.

Would reach out to @learnlikeaCPA aka Ryan Bakke who is an STR specific CPA that can likely help with the tax implications of this. 

Regarding what tools I use, I am just looking at rental comps to get my insight for specific neighborhoods.

I've owned a number of rentals, done some flips, minor land development, etc. in the past in Nevada and Yuba Counties (still have a couple of places in Smartsville), and am actively looking at new ops in Grass Valley specifically. 

What is the specific sentence of offense?

Develop housing solutions that cater specifically to the needs of veterans.

I'm looking to build a wholesaling business around SFHs here in Southern California (Riverside County, specifically), then expand in time to MFHs, possibly commercial.

**************************This specific deal you mention, does not appear to meet any promising criteria.