Handhelds are fine with some caveats. I've run with one for most of 4 years. Comfort is fine - first run it's annoying, second you don't mind too much, and after that you don't notice it. The good ones have straps that securely hold it to your hand so you don't even need to maintain a grip on it. Plus it saves your hands when/if you trip as it absorbs the impact. I'd not want to have two as I like having a hand easily available.
I recently switched to a hydration pack for trail runs over an hour and I liked the switch so much that now I wear it for basically all trail runs. For me, I don't even notice I'm wearing it (even less than with the handheld) and I love not having to think about water at all. The result of this is that at least a couple times a week I'll just go off and find a trail I don't really know and set out without a predetermined route or mileage and just explore whatever way looks good and find my way back when I feel like it. You can even throw a phone in it and a little bit of food or a light jacket. I keep a bladder on with water and usually take one bottle up front with electrolyte water. Usually just use the bottle but I don't notice the extra 2 lbs of water on non-workouts so I keep it there just for the freedom.
As for brands on packs, the Salomon ones are expensive and don't stand out on specs alone but I found they are much better designed, obviously by runners who use them a lot. The materials breathe better and are much lighter, and are elastic so the packs fit like a glove. You don't need to mess around with tightening different straps or points that rub.
Don't bother with the different fanny pack/belt options as those not only look dumb but the bottle bounces around and is by far the most intrusive and least flexible option.