Setting is a scifi star spanning nation on one end of the worm hole and an early sailing and early/pre gunpowder on the other end of the wormhole.
Hero is possibly part of an exploration corp and has a relative/love interest on the sci-fi part of the wormhole.
Hero goes through wormhole and ship starts failing and crashes on planet. Wormhole endpoint stops or inhibits technology.
Hero either has AI or some other source of knowledge.
Once crashed on planet hero involves himself with local nobility to help her? out of several jams. Builds a new settlement and builds a sailing ship. A catamaran if I remember correctly.
Hero ends up raiding/fighting invasion or slaving parties.
It isn't Pennlady (where is she anyone?) But I seem to remember it was a semi-pro or very talented female author from that era 5+ years ago maybe.
Maybe 3 stories in the series