Greetings Michael -
Lots of folks successfully do what you are in search of every week, be it POTA, SOTA, holiday trips, whatever, so I am sure someone will be along shortly to share some info.
In case no one drops by quickly, you might try the N3FJP Software Users group over in groups.io. Lots of AC Log knowledgeable folks over there as well as Scott (N3FJP), the author of AC Log.
Also, you will need to have a separate LoTW certificate for each of your QTH log uploads, as well as making sure that you have selected the correct one before uploading to LoTW each time.
There - I've shared all I know (but would love to learn more).
W4HRL
Mike in PoquosonVA