Self trenching shouldn't be too hard with the proper machine, if you are reasonably fit and have a handy friend you should be able to do it in a day or so. The trench doesn't have to be particularly deep or wide, installers in our area usually don't go deeper than 12" with cables in the yards. They used to do it manually with a splitting shovel for small jobs, now they use trencher machines. You only need a couple of inches wide and a foot deep trench usually.
The only issues are if you have many rocks or trees in the area, roots will present problems. You could rent a machine and try it.
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