Re: Southern Oregon
Jacksonville is pretty small and relatively quiet. It has become yuppy sort of which means real estate is a premium. I don't know what your priorities for a retirement place, but I am going to assume chasing fish is on the list.
Jacksonville will give decent access to Applegate river and lake along with some small streams upriver of the Applegate lake (carberry creek). You will also be in decent range of the rogue river.
Or you could look at the other end of the valley out towards Eagle Point or all the way out to Shady Cove. That will get you probably lower property prices, more golf. You will have access to the rouge river, lost creek lake and a little further out the S Umpqua river and a straight shot over to Bend.
Either side will give you fairly equal access to I-5 , the mall and downtown
***Why Flyfishing over golf ? You cant take your phone in the river***