As a first-time pool owner for about a year now, here is what I experienced with each type of cleaner. You can take away your own conclusions.
The PB included a pressure-side cleaner from a Tier 1 manufacturer (Pentair Racer) in the contract. The cleaner was hassle free. It did a good job picking up leaves, and even the small toys my kids tended to leave in the pool (like 5-inch long underwater torpedoes). This cleaner lived in the pool.
However, the Racer never climbed the walls, although we were led to believe it would. Not such a big deal. The biggest thing was that it simply would not pick up the 2-3 millimeter deep layers of fine red sand and grit that gathered around our drain covers (that I believe blew in before we had our sod replaced). Having said that, the Racer's ground clearance also meant it never got stuck on our drains. Ever.
I tried brushing the sand in the drains, it didn't work. And I wanted the walls climbed. So after four months of the Racer, we got a robot (in my sig, I believe). Worked like gangbusters. Climbed the walls, picked up the sand, never got stuck. The thing was incredible.
However, the robot was a REAL PITA in my case to put away. More like 30-35 pounds when wet, and getting it out of the water was just half the battle. Then I had to coil up the dreaded 50' cable, which refused to coil until the twists per foot in the cable were just right. Consequently, the robot soon started living in the pool, although the manufacturer says not to do this.
To make a long story short, after 2-3 months of 24-7 living in the pool, the robot quit climbing the walls, and started getting stuck on every drain we have. And now it is winter and there are big huge leaves that blow in from somewhere (I do not know from where) which are too large for the robot to pick up...and that's when it's not polishing its treads on a drain cover.
So soon, I will put the pressure-side cleaner back in for regular 24-7 habitation, order a replacement tread kit for the robot, and use the robot just once every few weeks or so, removing it (the robot) promptly afterwards, and putting the Racer back in. That's my story and my plan. I have a lot to learn still.