You are wise Scott to recognize the limits of comfort. Boat size could be helpful, but it is also an issue that too big might not be manageable by you as a solo sailor.
My Lyn, is not a sailor.

She enjoys the boating, and will manage the helm while I do all the boat management work, but not a passage and definitely not an over night where she is responsible for her safety standing a watch while I try to sleep.
At least not yet...
She is uncomfortable being on the water where land is over the horizon.
These are fears that may or may not be overcome. Only way to know is to, as you say, try it... In baby steps.