For my part, I always found the idea of the Federation agreeing to a legal ban on cloak development rather silly. Admiral Pressman was wrong to violate the law of the treaty, but there's some truth to his belief that non-development was putting the Federation at a disadvantage, especially militarily. It's even sillier in the context of the Klingon Empire (which uses cloaks on many of its vessels) no longer an enemy, and the Romulans are not going to be able to fight a two-front war against both of them in the event the Empire simply trades cloaks to the Federation. And we've seen holograms being used to hide things in way that, practically, is equivalent to a cloak.
That being said, I do think there are plenty of logical reasons why the Federation would choose not to utilize cloaks as much. The technology clearly has significant drawbacks and risks even after a century or more of being practical, and there are technologies that can penetrate the cloaking field. Using a cloak for stealth is handy when you need it, but you can only attack or defend yourself with weapons by turning it off.
There's also issues with a ship either sustaining damage that affects the stealth, or the design simply having inherent flaws. O'Brien commented that, in its initial configuration, the Defiant's cloak might have gaps because its power signature is very high for a ship of its size. And the first warbird in "Tin Man" sacrificed their engines in the attempt to reach Tin Man first, to the point where it bled through the cloak and they couldn't have gotten home even if they wanted to.
The FASA RPG had the useful suggestion that captured cloaks were generally rare, as the Romulans normally booby trapped them if they felt there was a chance of capture, and they typically weren't compatible with alien systems unless specifically modified (as happened with the cloaks traded to the Klingons). One Starfleet vessel testing a purloined cloak was never able to decloak, effectively disappearing forever.
