Do I just oil the heck out of it, or is there something else I can do?
Yep, clean, condition, rinse, repeat. Although I'd recomend not rolling the leather around until the conditioner has soaked in if you feel like it's so dry that it's going to crack if you do.
I don't think it will...I bought it for pretty cheap, put it on my horse, climbed on, and it squeaked it's way into giving me a headache.
Sounds like I have plans for this weekend...wine & oil! haha thank you