I love running with water! I know I don't drink enough water every day (FYI - we should all drink half our body weight in ounces per day, not accounting for exercise. Ex: I am about 120 pounds = 60 ounces per day, and more if I exercise.) I like to use my runs as a chance to really hydrate. And I get hot and having cool water is really refreshing.
Nathan Quickdraw Plus
My first handheld bottle was a Nathan. I copied Stephen's since I was/am an ultra noob. It was a great starter-bottle. Mouthpiece stays open, so you can really chug. Plastic is durable, but squishy. The pockets were totally rip-stop. There's a little "thumb hole" at the top of the hand strap, so you can adjust hand position. Minor complaints: mouthpiece stays open, so I would find myself forgetting to shut it and dripping water all over myself or pissed that I'd lost water on a hot, long run. I carry my phone when I run (I love being disconnected but I worry about safety and like taking photos of flowers). When I can feel my phone vibrate in the handheld, I have to unzip it to see what's up because the pocket is completely opaque. Also, the handband is kind of wide, and on my small hands I'd get some numbness in my fingers or soreness in my hand and wrist, but only on longer runs (2+ hours). I still use this bottle, but I've kind of transitioned into....
Ultimate Direction Handy 20
At first I was annoyed by the pocket and mouthpiece because I was used to the Nathan. However, now I really like both of those features. The mouthpiece (a "kicker valve," I guess) is always closed. To drink, pop it out and bend/chew it. I like it for two reasons 1) I don't spill Scratch water down my legs anymore 2) I can't chug, so I end up sipping smaller drinks over my run - which actually feels better on my stomach! The pocket is mesh, so I can see if that phone notification is important (like my new Hokas have arrived) or if I'd prefer to ignore it (oops, was I supposed to be in class?) I also really like that I can see through the plastic bottle. I get a little loopy on long runs and sometimes think I have more water in my handheld than in reality.
I'll definitely keep both of these bottles in my rotation. On long runs lately I've been running with a hydration pack (yay, hands-free!) But for shorter training runs it's nice to just grab a bottle and go.