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.