Peter, You're sure buying into a lot of grief if the spelling highlighted above was intentional!
If not, you'd better hope that your "wide" doesn't see the post!
On another note, I, to am interested in seeing what you get for your $300.00, as we are going to be doing that route next year, at about the same time. . . .
Ha! I mostly post from my phone with fat thumbs.
I have very little experience with rallies. My wife ('wide') and I have been together for years and love the cruising we've done, but, now retired, are looking at a much more extended lifestyle. It's been a long time since we've done something like this, and she's a bit nervous, especially about some of the physical aspects and being able to do overnight runs. She's also excited about visiting small towns and sampling local food and meeting people. I view these are normal concerns, and a rally would put us with many others with similar concerns and experience. It's a good glide path, at least for us. A couple weeks and some newfound friends and you're off to wherever you want to go.
From a practical perspective, I believe the greatest value a cruiser rally brings is weather routing. You can prepare for a lot of stuff at dockside, but weather skills take some trial and error to correlate what you expect with what you experience. Rally organizers chose seasonally beneficial times, and assist in forecasting what conditions to expect. By the time a boat gets to Cabo, they have a decent head start on making weather related decisions.
As mentioned, we had hoped to make the Ha Ha that starts in a few weeks (same time as Panama Posse and CUBAR). Instead, ad are looking at a Feb 1 shove-off, and will probably head fairly quickly to Mazatlan, perhaps Puerta Vallarta and leave the boat there for a while. We briefly considered CUBAR vs the Ha Ha but the sail-oriemted Ha Ha is more our style than CUBAR, even though as a powerboat in a sail-oriented rally, you're a bit of a stepchild. CUBAR seems to have a very strong sense of umbilical cord with mechanics, doctors, agents, etc. I had forgotten about Panama Posse so didn't look at that at all but should have.
When we leave, will be solo which is fine too. Weebles should be launched soon and we'll do some extended sea trials to knock the rust off our cruising chops - up to Catalina or perhaps to the Channel Islands (about 200 nms from Ensenada). Hopefully the old muscle memory kicks in for us both.
What is clear is the cost for these rallies is inconsequential for most boaters in this category. The value derived is highly personal. I'm ambivalent but thought it would be a good glide path for us as a couple. But since we missed the departure dates, will just make due.
Peter