I am so torn. This will be my 4th boat, so I am not a noob by any means. But I am not a mechanic either. I've had a 17' open bow with an outboard, a 23' cuddy, and a 27' cruiser in the past. But I am now committed to going with the flexibility of a trailerable runabout as opposed to something docked. I live in Rochester, NY, so trailering gives me so much flexibility to go to Ontario, Erie Canal, Finger Lakes, etc.
I had horrible luck with the 27' cruiser. It was purchased used but in phenomenal condition...or so it seemed (2004 boat bought in 2007 w/40 hours on the engine). But I had nothing but engine problems...literally from day 2. On the 2nd time out I had an oil pressure issue and had to be towed in. I should have gone back tot he dealer and gotten a refund right then and there...just like taking a toaster back to Wal Mart!

In the end, I had the cruiser for 3 or 4 summers, and ultimately another serious engine problem caused me to unload it before the winter at quite a loss. But I couldn't deal with any more worries about reliability.
So while I know I can save a small fortune on a used boat, I really think peace of mind is leading me to a new one. I am down to the H190 and H200 discussed here. Both are new 2011 models.
But I am also really really really really in love with the Cobalt 200. From a size perspective, it is more in line with the H200. It offers "arena" seating which we like. BUT, it is significantly more costly. It is not an apples-to-apples comparison because honestly the Cobalt does have several pretty nice upgrades over the H200 (very cool swim platform/step plus a duo prop outdrive). But that being said, it is still a pretty steep jump in cost.
Anyhow, my short summer in Upstate NY is slipping away and I want to pull the trigger soon (as in before the end of June).
I know...this is a GOOD problem to have...not complaining at all!