Sounds like you would be ideal owners of a Morgan (of any type)
You say you are used to quirkiness , well Morgans have that in spades , and then some. It is part of the reason that we love them so much.
Having said that some are more liveable with than others.
If you are ever on the West Coast then go to Morgans West in LA run by Dennis Glavis , or Isis Imports near SF run by Tcherek Kamstra (daughter of the founder) They will both have a selection of pre-owned cars for you to try. However I guess that Chicago is probably closer , so try Norb Bries at Northshore Sportscars.