We also have the 2008 model but looked at two 2005's in the process. You didn't mention if you were looking at a deep or shoal keel model. Our broker was representing all three 27's, the two 2005's were shoal, the 2008 was a deep keel which he told us had better sailing characteristics. We ended up with the 2008 only partially for that reason and probably would have gone with the shoal keep if one of them was priced right but we got the 2008 for less than either of the 2005's. All that said...........The boat had everything we were looking for in a coastal cruiser. It is basically the same layout as the h33 but a smaller package. We have the in-mast furling which was on our must have list, the jib is about a 105% and is very easy to handle. The PO owner ordered the boat with the optional winch package which adds self tailing sheet winches next to the helm so I can easily single hand the boat. It weighs almost 800 pounds more than the h306 and only 300 pounds less than our old Island Packet 27. It handles the Lake Erie chop and large boat wakes very well, we are also very pleased with the sailing characteristics. It motors well, the little Yanmar will push us at 5-6 knots at cruising RPM with the factory prop. The cockpit is large and comfortable, we also have the folding wheel which is nice at the dock or anchor. The rail seats are a big hit. The anchor locker is deep, we replaced the Danforth style that came with the boat with a Lewmar claw that lives on the anchor roller and is easier to deploy. Down below there is storage everywhere, the aft cabin is comfortable and airy with the two opening ports(also a box to be checked on our list). We use the V-berth for storage mostly. We like the chart table and storage under. The head is serviceable with a sink and shower. The galley on ours has the dual fuel stove and a microwave, neither of which was ever used. Hot and cold pressure water. We also have the electric cooler under the galley sink which works well. The walk through transom and swim platform were also on the list and there is a transom shower. Another thing that I really like is that all the seacocks are under the cabin sole at the bottom of the companionway ladder, easy to get to. Same with the transducers for the instruments, just forward of the table. Access to the diesel is excellent with hatches and the companionway steps on gas struts.
Downsides: I think the lifelines are too low and not safe. I would have liked taller stanchions, these catch you calf high. The electrical panels are horrible. I have never seen anything like them. Breakers on the front and the back of the panels are a way less than an ideal setup. Access to the battery charger is difficult, it is located behind the electrical panels so the indicator lights on the charger are always hidden. Cockpit storage for fenders and docklines is VERY small. As far as survey tips? Our boat was winterized when surveyed so he missed that every faucet and shower was broken by the mechanic that winterized the boat for the PO. I had to replace them all. Our 110v wiring was done incorrectly, the microwave and stove were wired to the breaker marked hot water tank, the hot water tank breaker was labeled microwave. We added a couple of fans, the main cabin can get a little close with only the front hatch that opens. The PO also ordered the highwater alarm system for the bilge. There is indeed a high water alarm with a float switch that activates an alarm on the cockpit instrument panel, however the big pump and plumbing that was supposed to be part of that system was never installed. Hope all this helps. Craig