I'm now leaning towards IB and wheel.
A wheel might be removed when docked or anchored (a tiller could also be kept out of the way)? And, a wheel may be more fun (there's some reason for its popularity). In any case, this is just where I'm leaning... I'll try to actually see one or more C27's this weekend.
Is an Edson wheel a good one? I read a couple of listings that mentioned this is what they had.
Wheels are more natural. Left goes left, right goes right, just like a car. However, tillers provide better feel under sail. I prefer tillers for that reason. Plus they're mechanically simpler. But you run into trouble the first few times out with new sailors until they figure out that tillers work opposite of wheels.
Tillers were standard equipment on most (all?) C-27s prior to the 270. Maybe some late model boats had wheels but I don't think so. The cockpit on the C-27 wasn't designed for them so most wheels out there on C-27s are likely retrofits.
Edsons are a standard retrofit. I looked at one for my C-27 until I saw the price tag. Keep in mind that with a wheel pedestal, you lose that cockpit space to sit on either side permanently even with a small wheel. The pedestal takes up a lot of the space between the seats. You'll understand when you board a C-27 equipped with one. At least with a tiller you can tip it up out of the way when at anchor to make room.
Wheels vs. tiller is personal preference. Go with what you prefer. On a C-27, I prefer tiller. On larger boats (and my next boat), I'll have a wheel.
How do we get a shower on a C27? Is it an original option? Or is it something that's added later? One boat had the shower in the cockpit (which is supposed to be better for drainage etc.). Does this require a hot water heater? Does such a heater come with an IB, or is it, along with some shower apparatus, something added? How would we add one? Are there places on the Chesapeake that do this work or do we buy a kit (I'm handy enough)?
Showers were typically aftermarket. I've seen some C-27 diagrams showing a shower sump in the head but I don't know if those were factory or not. Definitely not in the cockpit.
Showers don't require a water heater and no, they don't come with the inboard. They need to be added just like a household water heater and will draw power from the onboard batteries. Quite a lot of power too so you need a good size bank to run it.
If it isn't present it can certainly be added. All depends on your budget and requirements. You can do it yourself if you're electrically and plumbing handy or you can hire someone to do the install for you. Plenty of marine electricians on the Bay. Cover your wallet to keep it from screaming. It can get pricey.
Re: our 4 foot pier. The comments about this are noted. I'll take some more measurements this weekend and also check the tide. I do know that there's very soft silt at the bottom... soft enough that a stick goes right through it w/ little resistance for some further distance. A C27 seems the ideal size boat for us. And, the pier is my gf's dad's and being able to use it is an important consideration. His neighbor has a sailboat of similar size, and they have no problem... I'll have to ask about the draft on their's.
Keep in mind you aren't pushing a small stick into the mud...you're pushing 2000 pounds of lead fin attached to 6700-7000 pounds displacement sailboat into that mud. You tend to grind to a nice, gentle halt. Getting off is a challenge without high tide.
As for winterizing... not sure... is there a place near Pasadena, MD where we'd be able to take the boat and have it put on stands for the winter (and get any annual maintenance performed)? I'm guessing this is the case.
Lots of yards in the area and more in Annapolis or across the Bay in Kent Narrows. Google around and plot them out. Make sure the yard offers the services you want for land storage and the cost is reasonable. I tend to do my own work so that is a requirement of mine for storage. Not all yards allow do-it-yourselfers. Cost is also factor but generally the further you get from Annapolis, the cheaper it gets. If you're willing to sail and drive to the yard, rates and features are reasonable. I can make good and not-so-good recommendations depending on how far you want to go.