Relatedly, the Fairfield Metro (not ffld downtown) station is great for commuters. Enormous parking lot and it’s easy and quick to navigate/walk into the station from the lot… that may sound granular but in the mornings sometimes these little things make a difference! It’s much much easier than leaving from more crowded stations with packed parking like New Haven, and parking fees are low. If you don’t move to a town with a station right in town, this is still an easy station to park at and commute out of. It’s ~1h20m to GCT, no transfers.

If this person wants a richer town than Milford, as I recommended, than I would say go with Trumbull. Fairfield to West Hartford would be traffic heavy, since they have to get past Bridgeport first. The drive from Trumbull to the Bridgeport train station is really quick, and there's a parking garage (OP's post said company covers parking and the train). The drive from Trumbull to West Hartford is a little better too, and I'm kind of biased because I grew up in Trumbull, but I think it's better than Fairfield for a fraction of the price.