Ontario has the most anti landlord/tenant friendly regulations in North America in my opinion.

Overturned in King County Court, appeal pending. 2017 Rapidly rising cost of rental housing Rental Agreement Regulation amendment SMC 7.24.35,36,38 limits move in charges and requires provision of payment plan.

You will need to do a 506(c) if you wish to advertise and that is accredited onlyYou can do a 506(b) which allows non accredited but sophisticated but you cannot advertisePublishing info requesting people to fund a deal is not recommended since it violated sec regulations (note I am not an attorney)

You should not be considering being a landlord until you have done extensive studying on real estate investing and have also learned all of your state landlord tennat regulations.

Rather than calling the departments of real estate and asking if something is legal (they're not going to advise you on the legality of what you are calling wholesaling) READ the regulations on who needs to be licensed in that state.

Looking for a business accountant in the Southwest suburb area of Chicago that knows about real estate investing regulations, business taxes, and 1031 exchanges etc.

Obviously you would want to check with local regulations before entering in to any real estate purchase.What do you mean 1/2 of the year?

If it is by chance technically “OK”, it appears to me to be skirting the intent of the regulations around disqualified persons.Who’s name would the 5th Maryland LLC be in?

Basically, anyone who had a pulse could get a loan.In today's market, lending regulations are still pretty strict. 

Not deal breakers.I'm currently an active retail mortgage originator, amongst a couple other things, but Its been my experience that working as a wholesale account executive from 2000 until 2016 and being on the backside of literally thousands of loan closings since the inception of the newest regulations that I can recall only one instance of a set back caused by cents on a transaction, but that was early on in the Dodd/Frank era and was the result of software, that was subsequently fixed by an addition 3 day waiting period, because that was the safest play for the lenders ***.The take away here, again just in my opinion, is on the front side of the transaction, write the offer at whatever it takes to get the contract done, then hand it off to your favorite lender...they'll figure it out. :)