We had both a high end single jogger (Dreamer Design, sadly out of business) + separate trailer for our first, and then switched to a Chariot Cougar 2 for #2…
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I used both with infant inserts, but never with a car seat adapter (just not a fan of toting kids around in a “bucket” and used the car seat only in the car).
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Jogged at 12 weeks, didn’t ride until after first year.
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Every day that went by with the jogger + separate bike trailer, I kicked myself for not just buying a Chariot. We only have space to park the jogger in our garage, so having the bike trailer folded up in the basement was a hindrance to using it spontaneously.
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When running, I do find the Chariot’s low center of gravity harder to steer than a regular jogger (that said, that low-ness seems really appealing as my kids get older – they seem to think it’s more like a cool wagon since they can climb in/out).
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Depends on what “everyday” means. Heading to the zoo, going to open outdoor events, walking to your local Mexican restaurant and locking it to the bike rack so both parents can enjoy a margarita for once? Sure, even the double Chariot’s fine. Shopping indoors? No thanks. But then again, I see people bumping around stores with those all-in-one Graco stroller systems and they are freaking enormous. Really, I preferred carrying baby in a sling or carrier at first (they are so light! and even sorta snuggly.), and have since gotten a TON of use out of a $100 Maclaren umbrella stroller for those crowded indoor outings, especially for air travel.
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I walked or ran every single weekday throughout winter lows, but only ride in, oh, 60 and up. Yes, put down the rain cover in cold weather. Big fan of Patagonia’s buntings, both the fleece one and the puff one.
Also, either way you go, if you are at all considering having a second kid, consider getting a double now. It seems silly when you’re so focused on #1, but it makes things so much easier later (another point for the double Chariot since it doesn’t look at all silly to move the harness to the center and give baby a little more breathing room when the rain cover’s closed).
Congrats!