Hey @Isadore NelsonNYC’s tenant protection laws are strict, especially with rent-stabilized units and longer eviction timelines, so it’s essential to go in fully informed.

FHA appraisals are very strict. 

I don't know if this is true, however it would make sense that when you routinely pay down the HELOC, your interest amount declines and is not based on 6 month ave.

I was firmly denied and told, "we strictly do not allow short-term rentals, subletting, or anything similar".

If you routinely try to get the next tenant in so quickly after the last tenant, perhaps you can add a penalty to your lease for holdover tenants.

Is it better to purchase property as Vacation Rental STR, and then decide to switch to Long Term Rental if the regulations become more strict?

Those who have no cars or don't drive cannot simply walk into the parking lot to attend.If applied to residentials, such strict guidelines could mean (I hope not) nobody can be moved out of their apartment for any reason at all because all have to remain indoors indefinitely. 

But strictly going by the numbers, it's borderline OK, depending on the type of market.

Creative financing, partnerships, or shifting to long-term appreciation rather than strict cash flow might also help in this market.

Irvington is very similar to newark, which has very strict laws with regard to rent increases.