Unlike a cast iron skillet I'm having a much harder time keeping a pot clean and rust free. I use it mostly for roasts on occasionally some stews, any tips or difference in care between the two?
First I would highly recommend getting the food out of the pot as soon as its cooked. Letting the food sit in the pot for several days is the main problem. The sooner you clean the pot the better. I would scrape the pot (i use a polycarbonate scraper) to get it clean and then heat the pot on the stove to make sure is dry, then finally add the oil after you're sure the water has evaporated. When you apply another layer of oil it is not exactly seasoning the pot unless you expose the oil and pot to very high heats. I would recommend making sure the pot is clean and seasoned well, then try to follow the cleaning above.
As CrysOystr has mentioned, it's not seasoning unless you've exposed the vessel to high enough heat -- you actually need to polymerize the oil (basically turn it into plastic).
Heat your pot up in the oven, and then give it a smear inside and out with a good oil, then leave it to bake for about an hour ... then coat again ... and let bake ... and coat again. (I tend to do it while binge-watching TV shows, and give it a coat after every episode if it's hour-long episodes ... you just have to make sure it's British shows, and not those ~45 minute American shows once they remove the commercial breaks). After a season/series (5 coats if it's a 6 episodes ... the first one was just heating up the pot), you should have a well-seasoned pot.
When using your pot, you'll want to avoid tomatoes or things that are too acidic, as they might break down the seasoning. Once things are cooked an served, move any leftovers to another vessel, clean the pot and thoroughly dry it. If your oven is warm from other use, you can pop it in there to dry, and possibly give it another smear of oil.
Typically, the sides don't need to be re-oiled all that often if you season it well the first time. The problem comes from over-heating the bottom of the pot, and baking off the seasoning (either inside or outside). You can help prevent this by only heating the pan over medium heat when it's empty.