Before I comment, I’ll post the following disclaimer. I am a roadie, and before I had a mild stroke 6 years ago, I was good for 55-60 miles. I’m also a retired mechanical engineer.
So, definitely agree about the weight of the bike. Other than going up hills, that would also come into play if a lot of stop-start is needed for urban riding.
This bike uses the 7-speed Shimano Nexus internally geared hub. The knock on geared hubs is that they are heavy and less efficient than derailleur drive trains. However, for this type of bike, the weight of it and the anticipated riding, I doubt that this would be a problem. The Nexus is the 2nd tier to Shimano’s Alfine line of geared hubs. 3, 7 and 8 speeds for the Nexus versus 8 and 11 speeds for the Alpine. The gear range of the 7 speed is quite a bit shorter than what you would find with derailleur systems, but going back to the anticipated riding, this probably isn’t a problem. One thing to note is that even though the mechanism is enclosed, it is not perfectly sealed. Water and dirt can get in. Whatever Shimano believes is an appropriate maintenance schedule should be followed.
Not quite sure why a suspension fork is needed, given how these bikes are used, but all of the Winona bikes at this price point have them. That is a significant contributor to that 38 pounds.
Bike fit is always very important, even for a bike of this type. An ill-fitting and uncomfortable bike is clearly not good and can discourage one from riding. Working with someone who has some experience in fitting is helpful. One thing I noticed about this bike is that it has the old style quill stem. This will accommodate a bit of adjustment, but the problem is that if you need a longer one, they can be difficult to find.
This kind of bike encourages wearing dresses and skirts. Personally, I would always worry about catching them somewhere on something. I always wear appropriate riding clothes, bibs and jerseys, so there is no concern on my road bike.
All in all, this seems to be a serviceable bike at this price point.