unless you want to also spend time as a tourist. It also depends on how you want to spend your free time.  If you want to do outdoor activities, obviously the warmer months are best.
But I don't think any particular time of year is better for business, horndogs being horndogs irrespective of the season.

I would think mid-town is easiest for people to get to/ congestion pricing is $9- but if you are already in the city or taking public transportation isn’t a factor- plus if someone wants to see you is $9 going to be deal breaker- I don’t think so - hotel prices are up last year and are pretty high right now - prices are the highest in the spring and fall / then in December for holidays really get high -

I’m a touring escort and visiting often throughout the year and for the most part business is steady except it goes a little quiet in the summer. I am here now and would say business is good but hotel rats are a little higher right now.