So, I've finally made it all the way through this forum and I must say, I think everyone is pretty much in agreement that there is no one size fits all category. There are obviously benefits and detractors for every decision.
My wife and I are two years away from "retiring" ( at the ripe old age of 31) and going on an open ended cruise. I've been watching boats and prices and I have decided that the majority of what we will end up with will be based on what is on the boat when we buy it. There are a few items that I plan on adding regardless of how the boat is equipped though. My Admiral has made it clear that she would value a water maker, which I plan on piecing together. I also want to have a SSB with a pactor modem for communication to make our lives easier and reduce the amount of worrying our families will do.
Of course there are some niceties on my short list, like a small GPS plotter (Garmin 441s) and the Standard Horizon GX2100 (my thought being that the AIS will replace the need for radar in terms of being run down by large ships at night or in the fog). But if the boat already has an equivalent in good working order, I would hesitate to rip it out.
We'll carry the typical redundant battery powered alternatives, but we've worked hard to save enough to make this dream financially achievable and I know that it will take some restraint on my part to not load up the boat and deplete our "cushion funds."
There are a lot of well equipped cruisers out there, whether the PO gave up on the dream, or is ready to switch boats. Our biggest concern is where to get the boat. Most of the boats that have some of the gear we want (good ground tackle, cruising sails, some of the above mentioned gadgets) are located on the coast, while we are in Chicago. We'll have to decide if want to try to equip something here ( I imagine it might be difficult to find someone with a lot of experience installing SSBs in the midwest) or if we want to move a boat here to move onto it ($$), or do we rent a truck and take what will fit and drive right to a marina in FL?