This will be my first real season without renting gear. I've been on the hill 2 times and I can link turns, carve pretty decent, and hit a couple wide boxed, keep in mind this was all with rental shite. I not have my own gear and find it way more comfortable. Should I wing the first season and see how I do, or should I just hop right into lessons so I don't form any bad habits right off the start ?
If you have only been up twice and have not taken a lesson either of those times then you would greatly greatly benefit from at least one lesson right off the bat. It is very important that you start with a good foundation to improve on correctly. I think you would be surprised at certain things you will learn from a lesson you didn't know from just teaching yourself. It will probably feel like starting from square one.