I just received our permit approvals this week. 

When you say "According to county records, our home is permitted as a five-bedroom dwelling", that sounds strange. 

Who knows.Another option would be to buy a small parcel and slowly build a house with/for him and pull owner permits.

NY laws also require permit filing and permit fees.

Keep your licensing and permits in order, manage all vendor relationships with contracts and adequate insurance, maintain adequate insurance on your end and more generally operate your business soundly.

Provide them with any and all building plans, specs, permits, drawings, and quotes that you might have to help us get a handle on what your project looks like.THE FULLY-EXECUTED PURCHASE CONTRACT: They’ll need the contract signed by all parties to get the file into underwriting if you are buying the property.

You must analyze all the data (size of properties, # of properties of each size, location of best producers, regulations, # building permits for that size issued in the last year)3.

This was done BEFORE the city had a process to permit STRs.

It's a thrilling and rewarding world, but it can also be overwhelming for newcomers.

Note - the units without off street parking do have free, non-permitted street parking and there is always space right in front of the houses.