The city does allow for a waiver of the primary residence rule in special circumstances, but according to their own examples, they appear open to a waiver only if you can prove the STR is near a hospital and is "regularly rented in support of patient care" and that you've taken measures to promote the general thrust behind the law.

I appreciate everybody's feedback - @Jaron Walling this is definitely like being thrust into a no man's land RPG facing level 5 opponents with no XP and no perks!  

So I think it wise for folks to educate themselves as much as possible & grow organically instead of thrusting themselves into a bunch of properties just because they can.

January has two very promising educational events (more the main thrust; but, at an unusual pace, as far as I can tell) that look very valuable to a new investor - or to one new to the area.  

No better way to learn than to get thrust into the game!

@Steven Hamilton II,Yes - the structure I described is intended for people in multiple thrusts.

-you need to have a good team on the ground-you need to have access to non-traditional lenders (local initiatives banks/thrusts, local hard money lenders, even the city)-you need to understand your exit strategy is another section 8 investor-you need to be/think different-you need to look for people looking for long term renting;-you need to screen your prospective tenants like crazy-you need to be respectful , understanding, professional and by the book/letter of the law+letter of your lease, all-at-the-same-time!

I was thrust into the little puppy role that no one ever thought anything of.

In this article, I try to define what that means. https://www.biggerpockets.com/forums/52/topics/402...The reluctant landlords are sometimes thrust into a bad situation. 

Given that & the fact that a lot of these guys are younger & get thrust into the spotlight with much more money & notoriety than they are previously used to I'd recommend collecting a larger deposit up front as this would be a much more common situation then him living in your unit long term.