I'm also at a stand still to sell my Bonanza and get a Cessna P210. I know some of you will say I'll regretting the decision. I want something with a/c for sure, pressurization and deicing equipment is a plus. But like any plane you can keep on adding items and price just keeps on climbing.
All in all figure out what 85% of your mission is. Then go find a plane that fits the bill. Make a list of what you want or would like in it and go out and find the airplane
I'm 23 and would love to fly something from a Beech Staggerwing, to military aircraft, to faster and sleek looking jets. I would love to fly them all. They are all like ladies. Each one is different and special, but one will only stick around with you forever. I'm married to my RV8, but flirt with all the other aircraft...Come to think of it my RV8 is like a nagging wife.. always complaining about "check fuel" or "check fuel pressure"...She just has some bad sensors.
I love my Vans RV8, thought of selling her a few times, but will hold onto her until the foreseeable future. She's good for all the short hops I do, while the Bonanza or the future P210 will be better for the long haul.