The problem with Lee Loaders is that 7mm-08 is a discontinued model for some reason. If if was available I would say get the Lee Loader and a set of scales and go to town. I just don't think that the dipper is accurate enough and flexible enough.
Having been in your situation 3 years ago......new baby, no money, 2 rifles, 2 cheap scopes, I went with reloading equipment. You seem to shoot year round, so you will need it. Get Lyman #48 manual, cheap press, scales, whatever doodads that you want, Lee dies in 30/30 and 7-08, and some Hornady spray lube. You should have brass laying around, being the frugal sort that you seem to be......buy some bullets or I will send you some 7mm ones to start on.
Reloading is therapeutic like the man said above too.....new baby, no money, etc.