One of my guiltier pleasures is listening to an S.M. Stirling series from a David Drake outline,
The General series, aka the Raj Whitehall series. A lost colony amid the stars, a turbulent planet, and the happenstance hero with a computer side-kick coaching him through taking over the planet militarily & building back up to a high level civilization. It's pretty ridiculous & direct & simple, but something about it is comfortable & silly, relaxing. I should revisit; I have only read the first four books on the first planet Bellevue.
The Hammer Slammer series is the other go to name I associate with Drake (his books). I've been meaning to retry. I failed to get into the first book but hadn't tried very hard, was just a busy time. DD has a bunch of other series tok, would love more recommendations that have stood out to folks.