Our first "bigger" boat was a 32' Sundowner Tug - 23,000lbs, single screw, major amount of beautiful teak to maintain, complex expensive systems, expensive haul outs for expensive indoor storage, limited cruising area.
So, we had all that in mind when we bought our CD22. In fact, my normal method of doing things would have had me buying the CD25 but the above factors made me keep everything simple and easy.
Last year we purchased a motor home and kept the boat in storage (in-laws large shed). With "bigger" boat it would have cost us to store, some maintenance still would have been needed with teak, etc. With CD22, no worries.
We have everything we had on the 32' Sundowner (autopilot, house batteries, inverter, etc) but none of the complexity.
We cruised Lake Michigan and the North Channel with the Sundowner in 6 years. We have cruised Lake Michigan, North Channel, Erie Canal, Trent-Severn, Rideau Canal, Vancouver, Gulf Islands, Victoria and now stored and ready for next years San Juan Islands -- all in 4 years.
Buy the smallest boat you can afford.