Not really crazy. You have to start with a plan, no matter where/how you end up.That's what I am hoping.
Although who knows what the plan will be then.
3 years ago, swmbo and I were planning for a 42 - 44', suitably aged.
Wife much prefers 30'. Within her physical capabilities and I am starting to agree with her.
Now we are going down the path of 2 x approx. 30' cruisers, one for local sailing kept somewhere easy (and more expensive slip), I know our Irwin 30 competition is heresy but the restoration/modernization process has made us fall for it for coastal etc. Its a keeper for us.
The other would be a dedicated bluewater 30 ish'. Can be much further from the ocean, kept in ready to go mode.
When we get too old for bluewater, sell that, buy a stink boat for the ICW.
When we get too old for inshore, sell the Irwin and dunno, have no idea what the world will be like hopefully at least 25 years from now.
Probably sounds crazy to most.