I work for a CLEC, and I can't imagine a day without my Tempo Sidekick. The basic model (7B) offers a lot of great functionality. The T&N (transmission & noise) model covers all the basic features, plus loop current, loss, power influence and load coil testing. The Sidekick is a great test set, but it won't tell you about attenution. It can measure loop loss, but only at 1000Hz.
You might want to look at the 3M/DynaTel 965DSP. Nice unit with TDR features.
As much as I hate steering folks to other forums,
https://www.mccartyinc.com has a lot of info related to outside plant testing & DSL deployment.