As many of you stated, the server needs to upgrade. The problem is, I simply can't easily upgrade using our current host, and if we do upgrade there is a very likely chance we may lose many critical plugins. So I believe now is the time to discuss our options.
Option 1, try to move to Spigot and cross our fingers:
If we move away from Bukkit (Pretty much inevitable) we'll probably switch to Spigot. But sadly, not all Bukkit plugins work with Spigot and Spigot itself has very limited plugin support, and to double up on that problem my host actually does not support the latest version of Spigot. In order to get it installed, I'd have to manually compile it and deliver it to my host in hopes he has the technical knowledge to get it working on his end. It's a messy solution, but with the best possible outcome.
Option 2, Vanilla MC and screw all this fancy plugin crap!:
Switching to Vanilla 1.8 would be easy (in fact, we could even keep the map with little issue) but obviously that would mean losing all our plugins including our chat colors, wilderness, portals, dynmap, etc. We'd always be able to safely and easily run the latest version of MC though.
Option 3, self hosting;
I can reinvest the monthly payments to my host and put them into upgrading my internet at home, and put the server on a local computer. This will allow me to install Spigot, and basically do whatever I want. But, even the upgraded internet might not be as fast as what we have currently. But even at our largest, we've never been a "huge" server, even a standard home cable internet connection is good enough for what we have now.
Option 4, sit on Bukkit 1.7 a little longer and hope somehow, someway, Bukkit 1.8 happens:
Probably not the best option, but hey, it's still an option I guess?
Anyways, this isn't really a poll. The options are just ideas I have. Feel free to let me know what ideas you support, and what you're willing to risk and provide your own input into other possible options.