Ryan,
I'm a nearly lifelong islander, grew up doing it with my parents and we're lucky enough have our own place now. Our "big" boat is set up very in a very similar manner to Slickcraft's previous boat. (Slickcraft, very envious of that new Eastern BTW, very nice looking boat.) Here's some quick insight on the transportation questions:
1) Unlike those on the mainland, you have to use the boat to get to your place. There will be times when you need to cross the lake when others can stay at home. (Unless you can plan your trips only in good weather.) With time, you'll get to be able to pick an islander's boat out of the crowd at the docks; we typically have canvas up most all of the time and we favor older boats that have closed in bows as opposed to bow riders.
2) Islanders typically have an "all weather" boat that can deal with reasonable weather conditions (canvas / hard top) and often a second and sometimes smaller boat for quick trips, water sports and so on. (We have a 22 foot cuddy that's a true deep V hull with full canvas and a 17 foot Boston Whaler)
3) Everything that goes to / from the island will need to be transported by boat. We islanders also tend to favor open cockpit space and sheltered seating for this reason. Pontoon boats have come a long way from a few years ago and work very well for hauling stuff, I've seen several that have been modified to have full canvas. We had an 18" pontoon when we were building our place and it was handy for that. There are also a number of contractors around the lake that have commercial barges for larger items.
4) When looking at property, be aware of how it may be affected by varying lake levels, how wind and storms may affect your dock, etc. In the fall, it's very common to have strong west to northwest winds, also the water level tends to drop so look for rocks that could cause problems at lower lake levels. If you have to cross more open parts of the lake its's possible to see 3+ foot chop / whitecaps depending on the location and strength of the wind. If the neighbors have large stone breakwater structures protecting their docks, this is an indication that you'll be seeing some large waves from time to time.
If any of the above is starting to sound like work, you may want to consider looking on the mainland first. I enjoy the island lifestyle and quite honestly would not have been able to afford anything on the mainland that comes close to what we've been able to do on the island. As with many things in life, it comes down to choices and some compromises. Good luck with your search!