The easiest way to generate a map of all your trackables still requires way too much work. (Please comment or contact me if I'm missing a really obvious easy way to do any of these things.) Here are the steps to making an inelegant but functional map:
1) Become a Premium member if you're not one already. It's the only way to generate bookmark lists.
2) Create a new bookmark list and call it "trackables" or "bugs" or some such.
3) Under "Your Profile" on the main page choose "Trackables (Yours)".
4) You'll see a list (alphabetical by TB name) of all of your trackables. In the "location" column you'll find either the cacher who has your TB or the cache currently containing it. For the latter all you have to do is add each of those locations to your bookmark list. When another cacher has your trackable in their possession, you can either ignore it (since you really don't know exactly where it is) or bookmark its last known cache or event discovery location.
5) Under "Your Profile" choose "lists" and find your newly created trackables list.
6) From here you can open up the whole thing in Google Earth (this can be fun if you like virtual flying from spot to spot, but difficult to print a usable map from) or create your pocket query. I chose both, but the image below is from the pocket query. Once generated you'll be given the chance to preview it in a map; here's what I get:
Not very elegant, but it does tell you instantly whether you've found any of the caches in which your TBs are living. Of course, the metadata for each location only includes the TB name in a remote fashion (if at all); what you end up with is just a map of caches that have just one thing in common: they are hosting (or recently have hosted) one of your trackables.
A variation on this technique would be to bookmark the locations in a browser plug-in or cache app. The one I use most is GeoPrinter for Chrome; I also use it to make maps of the Great Detectives series of puzzle caches. The advantage here is it numbers the waypoints to make identifying them easier. Here are increasing zoom levels for my current trackable locations:
Here's what the same basic waypoint file looks like in Garmin's BaseCamp map utility: