Replying to Messed up shoulders

hokay so a year and a half ago i dislocated my shoulder for the first time.  skating, i suck at skating.  did my pt and everything they told me, it was fine until this year when it happened again longboarding.  i went to my doctor and he gave me the surgical preparation sheet, which i was not happy about.  since this summer, its come out more than 20 times, including multiple times pretty much every day for the past week. 
my questions are: how much permanant damage can i do to my shoulder by just letting it go for the time being and continuing skiing?  i really dont wanna sit out this whole season since i missed the end of last year, and the pain is bearable and i can usually ride after like 5 minutes of sitting out?
and how is the surgery for repairing a dislocated shoulder.  the doctor told me that its like 2 months in a sling, then 2 months of hard PT.  im concerned about my motivation to go to class if im fucked up or have to do a ton of physical therapy.
if i come up wtih any more questions ill post them in here