Why can't I just load all my music onto my iPod

I hesitantly got iTunes match and only because songs were not loading on my iPod because apple thought that I stole them. Some of those songs were loaded from CD's years ago and the CD's have long since been discarded or sold, some of those songs are original recordings I made (using my mac and apple software not less). They appear now with iTunes match, but my library won't load onto my iPod or phone and I'm not always around wifi (or wanting to use my data) to stream playlists…. why is it apple assumes we are all able to get onto wifi all the time in order to run our devices. I just want my music and my playlists to load onto my devices to I can play my music without having to select each individual song and loading it on while I'm on a wifi network. I would also like my songs to be intact, most stop half way through which makes for awkward moments when you're listening to the road trip mix you made and the songs stop halfway through.
iTunes match is a misfire and I'm sad that I'm paying for a service that made listening to music on my device a pain. This stuff used to be easy and intuitive and now its just frustrating.
fix this and help us out would ya?

The sync is one way - computer to ipod.  The only exception is itunes purchases: File>Devices>Transfer Purchases

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