There also isn't a clear guide if you need to evict the tenant during their lease how and if you have to reimburse NYC's HRA. 

Start today, before the problems occur, and your life will be so much easier.Do yourself a favor: buy "Every Landlord's Legal Guide" by NOLO.

@Jack PinardSend me a PM and I can send you my resource guide - it doesn’t format correctly when I put it in here

That conversation might guide how you approach the township about permits, but I would agree with Nathan that you'll likely pay some fines in addition to the typically paperwork. 

So I was in a hotel the other day with my wife on a trip.

Start with BiggerPockets Ultimate Beginners Guide (free).

As a realtor, I've guided many clients through their first property investments and I'm always eager to learn more from experienced investors.

A great step to help you narrow focus, budget, etc will be to speak with an STR focused lender.. contact @Joseph Chiofalo he''ll be a very patient mortgage guide. 

@David Niles thanks I'll check it out and reply@David Ramirez thanks I'll definitely check it out, might be a little far, but we've talked about heading out that way at some point just to see the city more, so maybe we'll make it a work trip

Guests coming in the following day for a $5,000 reservation and the client wants to shop quotes.Some people trip over dollars trying to pick up quarters!