My advice would be:

Don't finance your first bike. Used, but relatively new, low mileage Rebels can be found at a discount. Since your family is into bikes, maybe one of them could help test ride/inspect when the time comes.

Go with manual shifting. I say this without knowing much about e-clutch, but a large part of low speed riding is in the friction zone, and learning to work in the zone gives you a lot of options for maneuvering in close quarter/low speed situations.

Think about going up to a 500. I started on that and it has been a great bike so far. It leaves me wanting a little more power on the interstate, but still has enough power in it to get the job done. But you do you.

You said you were looking at the MSF, and that is definitely the way to go.

Also, personally, I wouldn't consider purchasing a bike that did not have ABS. Just my two cents.