Should be no different than using a PS2 or Nintendo. just connect the converter box's TV OUT connection to the VCR, make sure the VCR tuner is on Channel 3 or 4, then hook the TV to the VCR as you would normally, and make sure the TV is the same channel as the VCR/Converter. and use the Converter to change channels. you may want to invest in a universal remote control as some converters' remotes only control the TV and even some don't do that.
The Dish Network DTVPal Plus is capable of timer events so you can select through the program guide a show you want later to record, and the converter will change the channel for you and the VCR can record from channel 3 or 4 using its built-in timer.
If you have extra money and only use the VCR to record shows, there is a Dish Network DTVPal
DVR that allows you to pause/stop/fast forward/record live TV like the Satellite systems do. will save tons of trouble and only one device. but if you only use VHS movies with the setup you can just hook up the converter like listed above.
You can also use a A/V cable to use the converter with your TV and the VCR can hook up to the second input (normally on the front of a TV with A/V) and just switch between them if you have such a TV.