Taz, if you had that much trouble with breakage, you had a size too small or were really over tightening them.
AppyT, Abe might be ouchy without pads since a plain boot has a flat surface on the inside and he would be periphial loading, so dense pads would actually help more to build sole than boots alone.
To the OP, basically, if you just want to do some easy trail riding and easy application, any boot that comes above the hairline will do. They are generally easier on/off, but tend to be clunkier and more apt to get debris in them. OF course you can get wraps that help prevent rubbing, but if you really plan to do very athletic maneuvers, I would get something that fits below the hairline and has a pastern wrap. Less debris enters, no rubbing, and really, the cable systems don't usually break that easily unless you overtighten or they are worn out from use. You can put pads in any boot, and I highly recommend doing so, as it does help stimulate the soles. Besides Easy Care, there is a type of boot called Renegades that are pretty easy on/off and it's fairly open and allows dirt/gravel to come out as well as mud. They seem to wear a little faster than easyboots, but they are a good boot just the same. They also have more options in colors.
Almost no boot is recommeded for continuous wear in turnout. In certain situations, such as acute laminitis, it's better than letting the horse limp around, but you still have to take them off to let the hoof air out, and check for rubbing. Thrush will start to develop if left on 24/7. In a case of laminitis, or any time I would advise someone to use the boots for turnout, it's a short term basis. They are fine if you leave them on for a whole day to ride in, just take them off when you are done for the day.
When they are new and it's hard to get them on, put some baby powder in them, it helps some. Once they've been on/off a few times, it gets easier. For drainage issues, if you plan to ride through much water, you can drill small holes in the sole (usually voids the warranty, so be sure you want to keep the boots) or make existing holes bigger so water can escape quicker.
For sizing, it's better to have a slightly larger than too small size if your horse is one of those "in betweens" . Too small contricts the foot and the boot will break down faster. A little big and you can add a thicker pad help snug it down.