With an XTi you really just have to get a feel for it based on experience.
The problem lies with the VF, which has a lot of problems:
1. The VF on all of the 1.6X bodies (and especially the Rebels) is tiny. It's so small that it is nearly impossible to evaluate DOF. The only solution here is to move up to a larger format with a bigger VF, like the 5D. The 5D has a viewfinder that is about as big as what your would have gotten on a mid-grade film camera of yesteryear. The 1Ds is like a good film camera of yesteryear. Nothing matches the best film cameras from before like the OM-1.
2. Even with a big VF, all autofocus VFs make for poor DOF viewing. Because they assume you will be autofocussing, they give you a smooth grind on the AF screen. This smooth grind 'lies' to you about the DOF and even makes it hard to assess if you have nailed focus. You can solve this with a rougher ground screen like the EE-S screen for the 5D. Be aware that rough ground screens get dark fast with slow lenses. At f/4 it's pretty dim and by f/5.6 it's almost too dark to compose with. Rough screens and slow kit lenses do not get along.
And finally - once you get that rough screen, if you hit the DOF preview button at say, f/11, the VF will pretty much turn black.
While we are on the topic, also keep in mind that DOF is not a hard number. DOF is subjective and depends on how big you will print, how closely you will view the print and how picky you are. The standard DOF calculators assume 8x12 prints viewed at about 18 inches. If you print bigger you will need to stop down more. If you view your monitor at 100% from a few inches, you will need to stop down a ton as this is equivalent to peering at a 20x30 print from 6 inches away.