It seems insane to me, as my monthly recurring expenses are $375 before food, & $110 of that is Public Storage, so it's $265 once I move in.How strict is this 3x rule (OF THUMB)?

This requires strict discipline.

Trust me this is not worth getting into a legal battle over trying to make an exception, this is a business that is heavily regulated and guarded to protect all tenants rights.

Other states treat upfront rent the same as a security deposit, subject to the same rules, regulations and interest payments.

You have to be strict and tell them that the rent is due 5 days before the first of the month.

In this situation, could we set up a Land Contract such that my down payment would be used strictly to pay off the property taxes, and my monthly payments to the seller would essentially be equivalent to what I would charge a tenant to rent? 

I've been told to the best of their investigation, the title is clean.In NY, as I understand it, the state regulates title insurance.

I do have a pretty detailed lease stating housing regulations with roommates, and also had an addendum signed re stating the rules and how I will be enforcing them.But there is more to it, the individual had a friend over, whom barged into the females room while she was sleeping asking for a ride home, and on another occasion I was also told the problematic roommate was drunk walking around the home with JUST a shirt on, with all the goods hanging out.

It's a public forum, choose to follow the advise of posters with great care.Most investors doing rent to own, L/O and contracts have followed old methods for decades, most IMO are behind the times and while they can read things in black and white in federal laws, they don't always understand the intent, even attorneys have trouble in some areas of financial regulations.

"It looks like it is regulated that way for now because of certain SEC rules.