My $0.02...
Mine is a 38' FHB. I like diving, crabbing and fishing so I have a 13' whaler with a 35 hp Johnson 2 cycle. Totals about 850# on a Ross Kelly rated at 1000#. That said, we RARELY use the stern swim step. We side tie the dink once it's deployed and not in tow. We use a boarding ladder on the gunnel and it's great for boarding. Our dog is a bit lighter (at 9#) but I could easily see lifting maybe a 50# dog back and forth. As far as docking goes, I find it real easy to dock it by myself. My wife does not like doing the jump so I bring the boat in, get it into position, have my wife take the wheel and I slip over the side with lines in hand - without any jump to a slipery dock.
Regarding the sundeck - friends have one with no inside access from flybridge to lower helm. They have to go outside to get between stations, which in bad seas is not acceptable. That means that they have to stay at the flybridge which, in bad seas has the most violent movement. Personally I would stay away from this design.
Our boat has a 4'3" deep keel. We have full canvas, yet I rarely feel much of an effect from side winds when docking - some but not much (thankfully). Now current - that's another issue.
We have a gas grill on the stern (like most) but we use a 5 gal tank (instead of those 1# tanks). I got a "y" at the tank and have a second hose that runs to a Hr. Heater. With it on high we use our sundeck year round but some evenings when it gets to the low 30's we do find it too cold and have to go below.
Bayliner! Yea, I use to work there up almost to the point where Brunswick bought them out. Keep in mind that they paid their annual bonus based on material savings - think chopper gun here. Usually the guys in the shop became more "bonus consious" after mid year. If it were me and I had to have a Bayliner I'd target boats built between Feburary and August.
Knowing what I now know, if I had the chance to do it all over again I'd get a single engine sedan pilot house trawler with a large generator that could double as a get-home and it would have a bow thruster. It would have no teak or canvas on the outside. And it would have high bullworks. It could either be wood or glass but not both. (Just my opinion)