Wondering if anyone has a recommendation for a trusted carpenter/handyman/contractor who can install wood butcher block countertops?

Have your Contractor verify that pier n post is all code legal (looks like cinder block, no seismic straps, PT, in back looks like a 2x4?) 

I would suggest you also consider North Beach (yes, it's a neighborhood within the City of Miami Beach, but deserves it's own consideration for several reasons) and Edgewater (blocks from Midtown). 

Property is exempt from STR permitting because the jurisdiction considers it to be a commercial lodging establishment.We've been pursuing an SBA 504 loan for it, which was going well until we discovered that the sellers have operated it only part-time the last 12 years -- intentionally blocking 60% of available room-nights because they just weren't up for running it full time in their retirement. 

The boss is firm with it being Wildwood Crest only, very close to the beginning of the boardwalk, and 1-2 blocks from the water.

Yes - it's somewhat street by street when you go south of central but being within say 10 blocks of central ave you're still in a great proximity to downtown. 

That way the SSN is blocked out except the last four and I only get the full SSN when they go to apply after meeting the screening requirements.

So far I've notice some towns have regulations or already blocking STR like Woodstock, thing is that those are saturated markets already and no room for STR (IMO), but catskills is so big its a matter of a location and price! 

The total build is about 2,060 sq ft.We'll operate it as a STR and probably do $4,000 - $5,000/mo in rents and then have the flexibility to block it off for friends and family when they visit.I will say the process has taken longer than hoped.

It can go block by block, so having an intimate knowledge of neighborhoods is critical.The key is to not over pay in the more distressed neighborhoods, and to overfill, expecting to attract higher paying residents.Use this link for median income --> https://geomap.ffiec.gov/ffiecgeomap/Gino