Any recommendations for good cities within North America where there are high quality strip clubs where you can get extras? And then also a good hobbying scene? Ideally a mainstream-ish city to avoid eyebrow raises from the bachelor party members who don't partake.

My favorite is Tampa for this.  Great strip clubs and lots of providers!!

Im looking for the best options for a fun time now that Medellin is off the table thanks to global politics. Would you still recommend Tampa? Ideally looking to rent a house in the south east and hire some party girls / babes to party with us for a few hours with extras. Would you say Tampa is a decent option for that?

No doubt things in Colombia are fraught now, given the situation in Venezuela. But Medellin is nearly 900 miles from the Venezuelan border. But, yes, I'd think twice about going there even though I think it's a stretch to say it's "off the table" entirely.
If you have additional information about that, please share.

Jaco, Costa Rica

You’re spot on. Jaco is incredible. Unfortunately, it has the stigma and reputation that most know about. Looking for something like Jaco or Medellin

I've been there a ton and for months at a time between 2012 and 2023. It's beautiful, fairly cheap (though prices are elevated by all the Yankee $$$) and full of beautiful women from all over Latin America charging around $150/hr. If that's a stigma, it's one I've enjoyed a lot.

Oh I’m with you. The secret is out and the crew I’m going with, wives know about what Jaco entails is what I meant.

Blew their minds.