I'm a new poster so I understand if you take my limited experience with Carefree of Texas with a grain of salt.
I've been a member now for two short months and I don't think a weekend has gone by without fishing off the boat. I'm not going to reveal what I pay, but suffice it to say, it is very similar to what has been proposed above.
IMO, the problem people run into isn't so much with the club, but with an understanding of the costs of boating in general. Many of the boaters are first time boaters and they're going to bump into things. I feel much more confident driving the boat now then when I first joined, but just expect to have to repair something on the boat during the life of your membership. You won't be paying for fuel pumps and injectors, but you may end up fixing some cosmetic stuff or replacing an anchor.
They offer "carefree" boating, but there needs to be a very explicit contract in force for the partnership to work. I think this is where people run into problems about late fees, cleaning fees and the like. I was told (and haven't been charged yet, but I don't leave the boat dirty) that as long as you don't bring the back and it looks like a murder has taken place(lot of tuna blood etc...) you won't be charged. I haven't cancelled a reservation yet(and thus haven't paid a cancellation fee) because I follow through on my plans and wouldn't want another boater to not have access because I was too selfish. I'm quite confident you can cancel your reservation at the last minute with no charge, as long as you don't do it all the time.
I believe it is imperative to double check everything before leaving the dock! I always refuel before leaving (i end up putting like $4 of gas in the tank before heading out- im sure the marina loves that) so we don't run into problems later on. Always check the number of buoys, rope, life jackets and if an anchor is present. Utilize the dock staff to get familiar with the controls so you don't have any unexpected problems on the water that might require a tow.
As for the quality of the boats: I can only attest to the below 27 foot membership, but I can say that everything that needs to work on the boat does, and some other things don't. Like the 12V DC might be out...or a washdown pump might be clogged, but all in all, nothing that has affected our boating. In fact, it's probably the kind of stuff we wouldn't replace right away on our own boat. Safety items are always present(like life jackets and radio working, flare guns, air horns).
With this kind of membership arrangement, it is important not to wreck your relationship with management over something small or avoidable. Therefore, don't leave it in their hands to refuel the boat or something like that. I know we're the customers and all, but you make more friends with honey.
Apparently every Carefree boats is a franchise, with only a sliver of your payment going to the parent company. Every club is different so understand which club a post is referring to before generalizing. I can only speak to the Houston/Galveston/Conroe club, but I've been pleased with the availability and all.
If I had my own boat, I would be able to launch it anywhere (like driving it down to Port Anansas or something)
You can't really leave at the crack of dawn because the marina opens at 8 and closes at 8(on weekends) (although I've heard of people making special requests for 6:30- which might require a generous tip to the poor lad waking up early just to give you a set of keys.)
On that note, I would like to take a boat out to watch the fireworks on Friday night, but there's no real way to do this because you have to drop the boat off before then. Maybe they could offer some sort of night time drop off, but that would probably cause all kinds of problems.
The positives are numerous and listed above.
Hope this helps...