Savory, you asked a lot of great question! After thinking about those questions I really can't answer them totally.
The bike I have a got about 11 years ago. There is an old timer in town that fixed bikes sold old bikes out of his garage. I stopped just before I ER and asked him what in his shop would he buy if he was looking for a bike. He pointed at the one I bought. Off brand but was almost new and he gave his sale pitch so I bought it. It has served me well for cruising around in town I bike instead of drive when doing errands and small shopping ventures.
So, to be honest I'm just looking to get a new bike. I can't really compare or know what I want because I just haven't been exposed to different styles. As far as bike shops I would guess 5 hours away would have one but not sure either.
Assuming your use will continue to be around town doing errands, where I assume from time to time you carry stuff, you want to be sure the bike has braze-ons which are the holes to mount a rack. Or it comes with a rack with a weight limit that meets your needs. A rack will hold panniers of which Ortlieb are considered the best to have.
As for the bike itself, the material and wheel base (sports car vs luxury sedan) is a trade off between speed and comfort, like a car. The comfort bike will be a slower and slight more effort to pedal, because they are heavier then aluminum or carbon. But the gearing will still allow heavier bikes to perform well. For example, my touring bike does fine on 50+ mile days but it would be nice to have the steel magically change to carbon.
With e-bikes, the frame material is less important since the battery compensates. Most I have seen come with racks and the advantage of battery making them easier to pedal and go faster. if you don’t want or need the other Ebike features, such as the ability to take long rides/go up hills/ride further easier, then you might be overpaying for expensive features you won’t use often. On the other hand, as you age, the Ebike features keep you young. I’m doing fine without an Ebike for now but I did really enjoy riding one visiting a handful of wineries on my longest Ebike experience.
While there is more to consider, fit will be important for total comfort. If you need to reach too far for the handle bars, your back will no longer like you, Handlebar adjustment is done for height and reach Your saddle needs to be properly positioned. Hard saddles are typically more comfortable than the really padded saddles. People that tour who on their bikes for hours will often select the hard all leather Brooks saddle.
I tried to think of the key features. As some have suggested, bike store folks have skills to help you fit and to guide you to the features you need based upon the type of biking you do most often and your expectations on the bike. If you continue your research, I would try to figure out how you expect to use the bike and then do some of your own online research.
I have spent many years as a bicycle advocate. You look like a candidate to make your car a lonelier member of your family. So, if you have more questions, I’ll be happy to help you the best I can.