What to do with an oak wood high back chair, please?

silicon sliders on the feet of each chair will make them more moveable. the worlds largest on line retailer might have them, or office supply stores. you could park 1 where people enter the house, my place is a shoes off at the door policy (workmen excluded), one for each bedroom- a place to set out the next days clothes or the basket for dirty laundry/ needs repaired clothes. put one in the laundry area- again hold a basket while loading machines. kick a couple to the front porch after a coat of exterior paint or other out door finish.

Would you be up for converting them to outside furniture? so that you don't need to move them around so much?

If you wan t to keep them, then either use the sliders or cut a little off each leg and add rollers. If you want a different style, go to Craigslist or someplace and make a trade for what you want. I have some like that in a formal dining room that is basically for looks. I can put up with them not moving around easily. Good oak chairs are a great furniture investment and should last a lifetime-if that is what you want.

I would not paint them. I would make new seat covers.