I have all three bag types. The Players 5 will give you the room you desire for larger grips. I have normal grips and when carrying the Players 4 Carbon, I usually only carry 12 clubs. Pocket space can get tight at Bandon in December when carrying rain gear and 1/4 zip. That said, it’s my favorite for walking as it is the lightest and being a slim guy, fits best across my back. The Players 5 is not heavy by any means but just feels a bit bulky walking for a smaller guy like me. I also love the Carbon’s graphite legs where as the others have aluminum legs that sometimes get bent in soft travel cases.

I am currently rocking the Players 4 as I walk a little more than 1/2 the time. I too have midsize grips (Golf Pride CP2 Wraps), and they will stick every time getting them in and out. However - this is my only complaint - and it's such a minor inconvenience that is outweighed by the rest of the pros that my bag has to offer.

Weight and comfort for walking/travel - It's a little over 3# empty, and I didn't think that I would notice the 2# difference between my old bag, but it feels like I don't have anything on my back. The shoulder straps are fully adjustable and extremely comfortable. I can easily wear this on my back for a full 18 without any rubbing or chafing on my back or shoulders. There's a drink holder pouch if you need it, but I usually just toss my water bottle into my ball pouch so it doesn't fall out.

Top layout and how well it handles midsize grips - As stated previously, your grips are going to stick going in and out, unless you end up taking clubs out. My top compartment has D, 3W, 2i, and sometimes my putter. Middle two dividers are 4i, 5i, 6i / 7i, 8i, 9i, and the bottom has PW, 50, 54, 58 and sometimes the putter. My putter bounces between the top and bottom dividers as it will stick more with the bigger grip, and it's really just a matter of which slot is going to be easier at that given point. Again, the sticking to me is an inconvenience and nothing that would keep me from using this bag.

Storage differences (room for rain gear?) - I have a HydroLite 1/4 zip stuffed into the side pocket along with my rain fly, a bottle of sunscreen, and a zippered pouch that holds cards, tokens, pencils, cash, and a phone charger. There's room for a little more stuff in there, but with all the walking that's all that I keep in it. Ball pouch can hold probably 2 dozen balls if you needed, but I normally just keep 6 in there with a small valuables pouch that holds ball markers, my keys and wallet during play. The 24' model has a dedicated marker hole, so I'm able to quickly scribble over my provisional marks when questionable drives magic themselves on the right side of OB. The last pocket on the side holds extra gloves, another zippered pouch with extra spikes, extra tees, can coozies and a club wrench. On the days that an umbrella is required, I can stick one in the loop but it's a giant pain and falls out or slaps my butt when I walk; I usually just carry it because I'm more than just a piece of meat. I also have a Ghost magnetic towel that I wet before each round as well as a 20 x 40 dry towel that I keep looped through the carrying handle.

Durability and strap comfort - I've had this in play since last season, and so far the durability is impressive. I've walked probably close to 30 rounds with it and had it on the cart for another 30. The straps still feel new, the legs still pop out and retract nicely, and the fabric looks brand new.

Push cart compatibility — I've never put this bag on a push cart, but it does not fit extremely well on the back of a cart du eo the smaller size. There's no cart strap, and the shape of the top cuff is slightly elliptical, so it wants to roll when pressure is applied with a cart strap. Is it the end of the world? No. Annoying? Yeah, but it's not something that is going to make me switch to another bag for my personal time split between walking and riding.

I have traveled with this bag twice in the ClubGlove College with the Stiff Arm with zero issues. I took the heads off the woods and wrapped all the irons in towels, plus was able to throw in a couple extra pairs of shoes, balls, hats, and other clothes without any problems.