Bike/e-bike recs for renters with 1yr old?

I've been biking around Boston all my life and love my 2 speed freak-custom bike but it's definitely not for a kiddo seat. My wife also needs a new bike and is fairly small and intermediate at city biking. She is considering an electric bike built with the kidseat in the back but we have some concerns:

1. We have verry limited space in my landlord's driveway and no rain/snow cover so the thing is usually exposed to the elements. Are there any e-bile users dealing with that?

2. My wife is a bit forgetful and I can easily imagine her forgetting to charge the bike. So if we go e-bike we need one that doesn't turn into a ton of bricks if the battery dies.

3. Lugging a huge battery up our flight of stairs is going to definitely reduce charger usage. I may be able to get the landlord to let us setup a permanent outdoor charge plug setup. Anyone do that?

4. My wife cannot get over the fear of having the kid in a front bucket or rear trailer. So it needs to be a back rack style.

I feel i could probably survive with any old 7-21 speed commuter/mtn with a yepp on the back. But if folks have specific suggestions for e bikes that could work for us we may want to get two.

Thanks!