To Glass or Not To Glass...

I'd suggest a single for your first airplane. As for which year, it is
up to your budget. Aircraft are like cars in that the newer ones
depreciate more, so you will eat it when you sell if you buy new(er).
Still, safetywise, newer is better. Old stuff is OLD. If you like the
182 and glass cockpit, get one of those. Not a bad choice. Cessna 182
will do your mission. You'll just have to live with over the water
single issues, but Catalina can be flown so you can glide to land, if
you climb high enough. Small twins are expensive, and statistically
more dangerous than singles. If budget is at all a consideration, stick
with a single. Buy the newest you can afford.