Rolling Hills RIP my shoulders

Hi all, I've been using a hospital chair for 6 months but am looking at getting a proper chair because the injury only happened due to my EDS and I may potentially be showing symptoms for CANVAS which runs in my family, that's to say I don't know for sure that I'll need a chair permanently but for all intents and purposes it appears I will, and I will need to consider hypermobility and neuropathy in my choices. There may be a world where I can walk again with the normal amount of pain I used to have but idk, my Dr doesn't seem hopeful.

So the issue is I'm in a hilly af city. We don't have real flat sidewalks with real curb cuts, everything is just a severe slope with the bumpy ramps at corners only, most sidewalks and streets involve at least a 20° tilt either upwards or side to side. It's horrible but entirely intentional as they just redid downtown to be this way, gods knows why.

I went out to do a craft fair with my husband and had an absolute hell of a time just crossing the street and not veering sideways off the sidewalk into the street. I know part of this is attributed to the fact I have a hospital chair, the axle is too far back, I'm tall so I need my seat higher and I don't have a good range to push the wheels, it fits me as well as a hospital chair can and it's not good lol.

But I think even in a lightweight chair I would have a hell of a time with just how hilly and angled my city is. I've seen other people post about similar issues and have read through comment after comment trying to learn from what people have previously shared but I just thought it might be good to ask in case anyone has any tips or info I haven't seen. Or someone else who needs this thread will see it and get good advice even if I don't learn anything new.

So (TL;DR) is the only option for a hilly city and bad joints a power assist? Are there power assists that wouldn't be good for this? I worry my insurance will only want to spring for an electric chair because of my wrists and shoulders, but my understanding is electric chairs suck with uneven ground? I don't know anyone in my city who uses a chair, at the craft fair there were a handful of people being pushed in hospital chairs or using electric but no one self propelling in a manual so I wonder if that's just because my city is awful for people in manuals? That can't be a thing tho, right?