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To legalize a curb cut in NYC, your first step is to hire a licensed architect or engineer.

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.

It couldn't hurt to call a couple attorneys right away to see what they say in terms of cost and suggestions for dealing with this quickly.In terms of mitigating any legal issues with your tenant be sure you are documenting every conversation you have had with the HOA in terms of asking them to make the necessary repairs.

Looking to talk to someone who’s had experience adding a bonus room/sunroom in San Diego. Need some advice and some recs! Image for reference.

It just takes good design.

How keep it legal of course but more importantly how to do if effectively.

My designer just did a similar size refresh for $1500 fee and $2500 in materials. 

Maybe they've been burned by landlords in the past and are being very careful.You can legally reject them based on personality, facial tattoos, body odor, or other factors, but you better make sure you can prove that it wasn't based on any protected class like race, religion, familial status, etc.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.