I got my Concealed Carry permit in New York in 1970 and New York City in 1971.I carried a 2" Chief Special initially and then switched to a Walther PPKs. In those days we might have a group, go to the range, which was under a bank and since there were no ATMs in those day, we might walk into the bank with maybe a 6" model 19 in a holster on my hip out in plain view. All OK in those days. Now in New York if your gun can be seen when not needed, it is grounds to have your permit revoked.
After carrying for decades and NEVER having to Clear Leather, i just stopped based on all the current day restrictions. And I don't just mean New York, which I know most will jump on.
School Zones, Government Offices, Banks and a lot of retailers band firearms. I know, just wear it and don't say anything. I might try that in PA where I have a concealed weapon permit, but I am certainly not going to risk violation in New York with the Sullivan Act.
In any case, I am 71 and have lots of underlying health issue, but still survived a bought with Covid 19 over the pst three months. (I know New York is the epicenter), so I think the changes of needing to be armed are less than what I thought in the past.
When I owned by gun shop I had a big poster on the wall with a picture of an S&W Model 36 that said, "Its better to have it and not need it then need it and not have it". Maybe so, but not worth the bother for me.
Bob