If you want faster navigation of your basemap, or you feel that more than a couple of users will be requesting maps simultaneously from your server, you should create a tile cache of your basemap. You may also choose to cache thematic layers if their features are not constantly changing attributes or position.
In both cases, be aware that the tile cache represents a snapshot of your data at the time the cache was created. To put it more bluntly, your tiles are “dumb images” that will not automatically update themselves when the back end data changes. You are responsible for periodically creating new tiles in order to update the map.
With large caches, sometimes server administrators target the cache updates at just the changed areas, rather than rebuilding tiles for the entire map. This requires keeping some kind of log about which places were edited, or comparing “before” and “after” versions of a dataset. Later in this course, you will see that OpenStreetMap.org works in this way. If you make an edit to OpenStreetMap, you'll see your changes appear within a few minutes (at least at the largest scales). This is not because the entire cache was rebuilt, but because an area of change was detected, thereby triggering a partial rebuild of the cache in just the modified area.
Is there an existing tile cache that meets your needs?
Building a tiled basemap requires lots of rich data, high-end map authoring software, cartographic skills, and potentially enormous amounts of time and disk space. You may still need to do it at one point or another, which is why you will get a taste of this experience in Geog 585. However, because of these challenges, general-purpose web mashups often use tiles made by somebody else. OpenStreetMap is an attractive option if you want free tiles with no restrictions. If you want to use Google's, Microsoft's, or Esri's tiles, you may be able to use them for free, or you may have to pay, depending on the nature of your map (commercial or not for profit) and how many people use your app. Other companies such as CloudMade and MapBox have marketed their own versions of tiles using OpenStreetMap data.
If you are going to build your own basemap, it's helpful to have an experienced cartographer on staff who is experienced with designing at multiple scales. The symbols, colors, and details must be adjusted appropriately at each of the scales where tiles are created. Tiled basemaps can quickly get complicated with layer and labeling scale suppression rules. Cartographers may also need to design one set of tiles to stand on its own and another set of tiles to overlay remotely sensed imagery, a task that requires very different colors and symbols.
Projection
If you are going to overlay your tiles with any of the tiles from OpenStreetMap, Google, Microsoft, or Esri (or even just attempt to look like them), you must warp your most precious GIS data into a modified spherical Mercator projection that was created solely for the convenience of fitting the world onto a set of square tiles. GIS purists balked at this idea and predicted it would fail to achieve mass uptake, but many people (at least at mid-latitudes) now hold their nose and move forward with it.
Be aware that Esri, Google, and other organizations have used other code numbers and variations of this projection in the past: things can get very confusing if you are using older software or APIs. In the past couple of years, people seem to have standardized on EPSG:3857 although even the subparameters of this projection can be interpreted in diverse ways that lead to offsets. As a side note, can you figure out the humorous reason that Google once used the code 900913 for this projection?
Even when you display your maps in EPSG:3857, you do not ever want to perform measurements in this projection. The results will be largely skewed even at mid-latitudes. It's best to make sure that geometries are projected into a more local coordinate system before performing any measurements. Most popular mapping tools such as Google Earth and the ArcGIS.com map viewer do this behind the scenes when you use their measuring tools, but it doesn't happen automatically if you're building your own solution.
Scales
Not only must you match the projection in order to overlay, you must also match the scales. These are not nice, well-rounded numbers; rather, they were derived mathematically from the starting point of putting the whole world on a 2x2 grid of tiles. For example, one of the scales is 1:36,111.98 and as you zoom in, the next one is 1:18,055.99. So much for your simple USGS 1:24000 series! Partly for this reason (and partly because many laypeople don't understand map scales), the common web map scaleset is often referred to with simple numbers such as “Level 14,” “Level 15,” etc., that increase as you zoom in. You just have to get a feel for which levels correspond to national scale, provincial scale, city scale, neighborhood scale, etc. The table in the Bing Maps Tile System article is helpful for this.