I graduated highschool when I was 16 (that was 4 years ago , I am 20 now) , right about that time , one of my friends had called me and asked if I knew anyone who would be interested in taking one of the rooms in this 3 bedroom 2 bathroom house that he had found up in the mountains (Big Bear , CA) , its about 2 hours away from los angeles / orange county , where i was at the time , so I told my parents about it and they thought it would be a good experience for me ( Ive always skateboarded growing up and I figure snowboarding would fit just like a glove, so they offered to pay my rent for the 6 months that I was there ( for an graduation present)...fast forward , November to April - 6 months of working in snowboard rentals / having the best time ever / dealing with living alone at 16..
it was a good life experience..
I moved back into my parents house right before I turned 17 (may) , the season ended in April, so I got a job at this home loans place called Homeowners Friend, I was in the call center making cold calls following a script off a computer screen , the main goal was to get the customer to refinance with our company, so 3 months of that, I get promoted to Jr. Loan officer, w00tz , another 3 months after that , it was december 1st , and I just received my RE-Hire packet from the mountain , cause they wanted to know if I was coming back..and by that time I had already banked about 5-6 grand from financing home loans.. ( it was great money before the sub-prime market crashed)
btw , one of my close friends came up and stayed in my living room the last 3 months of last season , and then me and him both got a job at the home loans place..
so me and "said" close friend.. talked..and decided we weren't done with the mountains just yet( we both had gotten significantly well at snowboarding) ..so me and him started driving up once a week , going to different renting agencies ..looking at listings for some cheap 2 bedroom places..and we finally settled with this nice 2 bedroom 2 bathroom small place about 2 minutes down the street from the parking lot of the mountain ( which worked out well because I was over snowboard rentals and decided to switch positions to "Terrain Park-Staff' and we basically got to the mountain at 5am (sometimes earlier if it snowed , cause we have to get snowmobiled upto the top ( the chairlift isnt running at that time) and they drop us off with a big metal rake and we would snowboard down to each feature , sometimes its a slider-box , or a handrail , but it would be covered in snow , so we would spend about 15 minutes or so at each feature cleaning it up , making a take-off and crushing all the "snow-cookies"(big chunks of ice) as we like to call it , generally prepping the park for an 8AM opening..anyways
so we snagged this house for 850$/month / $1250 security deposit (utilities not included) , got both our names on the lease ( which if you ever go into a situation where its you and 1 person make sure you BOTH get your names on the lease so your both held responsible for what happens ( even tho were under 18 we had our parents help us out with those discrepancies... so we start moving up all our shit, meanwhile im calling the different utilitiy companies trying to have our gas, water & electric turned on for the season ..paying the 125$ gas security deposit..the 100$ electric security deposit (water was standard)... which is such a bitch to do so keep in mind if you dont find a place with utilities included you might have to follow those steps..
so Fast forward another 6 months...the end of the season is coming and the temperatures are climbing the thermostat..were getting ready to part-ways with our humble abode, ( this is pretty much where shit started to hit the fans) during the seaons things got pretty crazy..lots of partying etc..( 2 young kids with there own place up in the mountains does not call for a good mix ) so the front window of our door was punched out..some holes and chips in the wall from falling snowboards ( we would have like 10 of our friends come stay for the weekend and they would bring all the gear and shit inside the house..( and its just a 2bdrm / 2bathrm place so things got a lil tight in there..generally we just left the place a mess!! , at such a young age the responsibility and upkeep of this place didnt seem to be our top priority, so me and him bounce (thinking we did a decent job at cleaning the place before we left....we were sadly mistaken..) we get a call telling us we will not be receiving any of the $1250 security deposit that we put down , and infact owed about 300$ in other damages and what not..(CRAP!!!!)
so..may is around the corner..and my 18th birthday is approaching..I end up moving back into my parents house..got a job..and that was the end of my mountain escapades ( ended up not getting re-hired at the mountain due to my lack of commitment..which was completely my fault for taking advantage of such a great situation I made for myself..
so all in all..I guess I would say they were the best 2 years of my life and defiantly came out of it with some great life experience..
and to talk about what you had asked, I would do it again in a heartbeat just to have that experience again..
*here is some pics to give you an idea of what it was like for me*
this was the house I told you about for the first time I moved up 
My Room + living room ( thats the living room my friend spent the last 3 months in )

this is me and my roomate ( im on the left with the white shirt on)

so that was the first year..
here is the house me and my friend got the 2nd year


here is our crew ( im on the far left with the bandana on , my roomate is the guy in the black beanie u see upfront

us doing our morning stretches before we open the park

this is probably the best shot I got of myself all season