If it discharges 5 foot from the building and there is a low spot running back to the building, then it is going down hill back to the building.

Fines for unsolicited calls and texts run from $500 to $1,500 PER CALL and there are a lot of attorneys out there looking for people like you to sue.  

Here is a video that runs down the basics - https://s-media.nyc.gov/agencies/specialenforcement/01-Legal...There is also a prohibited building list - https://www.nyc.gov/site/specialenforcement/registration-law...Here are some more info overall - https://www.nyc.gov/site/specialenforcement/registration-law..All of this makes STRs in the city pretty tough but it certainly not impossible.

We have VAs that use triple line dialers and Pipedrive to run our CRM. 

Again, you're running a business.  2.

Run numbers and if they work do it!

I was told by another investor that I will run into a seasoning problem, but i don't see how if i don't plan on refinancing.

I can run and model numbers and am a CPA so comfortable with the finance side of things.

Quote from @Brandon Croucier: Financing a commercial MF that runs as an STR is possible.Appraising a property based on the income is not, whos to say a buyer would STR the property. 

I did run the numbers and it seems I'd be accruing more debt with higher mortgage than currently.