Hello jdiane:
33 years old.  Those were the days when vacuums were still a worthy appliance purchase for the ages.
I agree with Venson.  Probably the Kenmore over the HOOVER for $250.  Hovever, I would also suggest that you shop one/more of your local vacuum stores for a better canister vacuum than you can purchase in one of the big box retailer stores.  Test/try the SIMPLICITY canisters [mid size], BOSCH and Fuller Brush.  I think you will be impressed with these compared to a HOOVER/Kenmore.  Perhaps even a MIELE display model, slightly older model. 
Your Kenmore cann is good for a second or hand me down.  Your local vacuum store[s] can assist with parts and repairs on it.  Another reason, now that I think of it, of fostering a business relationship with a good, reputable, reliable local vacuum store.
Carmine D.
of the above names you mentioned[ .bosch-simp-fuller ]..how would you rate the uprights in the under $500 range.