Re: macgregor 22
Everyone is different, and I'm far from an expert. But... The one regret I have is buying a "stepping stone" boat. I bought a 27' and now want to upgrade after just a season and a half.
I did look at a 30' and that extra 3' made me nervous just standing at the helm in the slip.
Sounds like you have the basics down. I'd find a friend with a larger boat and sail with him a few times. Then buy something large enough that allows you to do what you want to do in 3 years.
If you know all you want is a daysailer or something for quick trips like on a small-ish lake, then disregard everything I just said.