They designated certain streets not for STRs and others for STRs.

They seem to be trying to use a PMC model designed for Class A properties/tenants for Class B, C and sometimes D.Can't use the same business model for all classes of properties/tenants. 

Design 6.

Then you'll need to find land, acquire it, find a spec home buyer and set up meetings to design plans or buy a set online with mods.

Retirement accounts are designed to be invested passively so when the IRS sees you running an active business in it, to level the playing field between retirement accounts and other business the retirement account incurs UBIT. 

What I can also tell you is that as an owner in NY, the landlord laws are very much designed to protect a tenant as opposed to here in Detroit where the laws are designed more fairly to protect both the tenant and the landlord.

I've owned the house for few years and have spent a lot of time trying to design an addition to add value to the property, but the current floor plan is really not conducive to realizing a return on that investment (tiny living room, low ceiling basement, poorly placed basement stairs, etc.). 

A good designer and architect are key for a successful project like this and keep in mind these aren't cheap.There's a lot more details to consider, feel free to DM me for more details.

For bookkeeping purposes, I recommend designating a separate bank account exclusive to the house hack activities to keep some sanity.

.: Stessa isn't good for keeping track of tax deduction items.Stessa was designed to just look at P&L.