Is that your avg cadence on the road? Spinning faster will help. I spin between 90-100 rpms. My SO is a masher and I'm miserable when I ride behind him. I can handle a headwind easier riding by myself, maintaining my cadence, than trying to ride his low cadence.

Also, check out the Cincinnati Cycle club. They have some beginner rides that are flatter and shorted distances. The Tues pizza ride out of Neisbett Park and the Harrison's Tomb ride were my favorites. The Pizza ride has speed groups and are "no drop". The Harrison Tomb's ride is an out and back and reasonably flat. I loved that ride because it was near the area that I grew up.

Yes, the trainer is a start. You need a good base of flatter miles before you attempt hills. I spent a lot of time on the Loveland (sorry, Little Miami) bike trail in the beginning of the season.