My dad and I are planning a roadtrip for October 17-27. We're torn between southwest Ireland and the Scottish highlands and online reports really vary. It looks like rental cars are available both places (haven't checked on accommodations yet). It looks like October is one of the rainiest months in the Highlands but that seems unpredictable -- not sure it's worth planning around. What recommendation would you have and why? We would want to hike and explore small towns.
In either place, you need to plan for and be prepared for rain. Possibly a lot of rain. Take this seriously.
Nobody can predict the weather with much accuracy more than a few days ahead. Both of your target locations have weather that often turns nasty in October. OTOH, you could get lucky and enjoy clear skies and unseasonably warm days. But you can not count on that.
You have picked two different places that both can get really soggy in the fall. Bring appropriate rain gear and footwear. Maybe you'll get lucky. More likely you will get wet.
That said, if going in late October, I'd probably take my chances on the southwest of Ireland rather than the Scottish highlands. At least in Ireland, the elevations are going to be near sea-level. Any precipitation you encounter there (and it's likely you will get at least some) will be liquid. In the Scottish highlands, it could actually be snow in the higher passes.