Sailing is something we have in our blood and the work involved is a labour of love. I am not rich by any stretch but I really wanted a sailboat and all I could afford was a MacGregor so I bought it brand spanking new. It is still a lot of work and major cost for accessories and it never stops, the time work & money invested I mean. I spend every extra penny and every extra minute I have with with my boat and have absolutely no regrets. You could not find a drug legal or illegal that can do for you what an afternoon on the water with just the sounds of the wind and water will do. The entrance fee is a passion for sailing, the rest is just stuff. If you don't have it in your heart you don't have it at all.
Go charter or rent or bum a day of sailing somewhere to discover what the end result of your efforts will be and decide from there.