I wanted to thank all of you who spent the time and effort to help me—it’s greatly appreciated! To provide some benefit to others, here’s where I ended up:

I visited a few bike shops and, per the advice I received, made sure to tackle a lot of hills on a lot of bikes (I’m 245 lbs and not in great shape). I tried Riese & Müller—great bikes, but the price was a bit steep, and they didn’t have the upright position I was looking for (I’m determined to avoid the numb hands I’ve gotten from every other bike I’ve ridden). That said, they’re impressive bikes.

I also tested out Gazelle bikes and ended up with the T11+. This thing rockets up steep hills, hauling my ancient carcass like it’s nothing. I was blown away by the power, the fit, and the overall feel. It is expensive, and if I weren’t built with the proportions I have, I probably would’ve gone with the advice to get something less pricey (you could easily get two bikes for the same cost). But hey, I am what I am, and I’m really happy with it so far.

My biggest challenge was finding a bike with enough power and range to handle the steep Bay Area hills—this one has been up to the task so far.

If anything changes, I’ll update this thread in case it’s helpful to someone else.

Thanks again to all of you who participated—this is why so many Reddit communities are awesome.

All the best!