I'd recommend buying what feels the best to you. You're not likely out there looking to keep up with a paceline or looking to score King-Of-The-Mountain times on Strava. If you're like most Cypress buyers, you're probably looking for a pleasant-riding bike that you can ride recreationally on mixed surfaces. Either Cypress model (the base model or the DX) will do that very well. There is a rigid fork version of the Cypress with rim brakes if you prefer it, but there's nothing wrong with the Cypress' suspension fork. It is heavier than a rigid fork and it will add comfort to your ride in certain circumstances. There are both benefits and drawbacks to anything and suspension forks are no exception. Some people don't prefer them for where and how they ride and that's great. Some people do prefer them for where and how they ride and that's great also.
So try both versions of the Cypress and see what you think feels the best. Maybe you can't tell a difference and you might like to save the 100 bucks. Maybe you can tell the difference and are happy to pay the $100 difference to have the fork or the disc brakes.
The Escape line has rigid forks, but the riding posture will be more aggressive. The Roam series is similar to the Cypress, with suspension forks, but they have a slightly more aggressive nature.
I agree with you that the bike shop makes all the difference, especially if you know you are happy with one vs. another. Trek bikes are also good, and the parts are pretty standard. All the bolt-ons are commodity items. Giant even builds many of the frames for Trek under contract. So the bikes, generally, are awfully similar in terms of quality of materials -- just ride different choices to see what feels good to you and which one makes you smile. That is the one to buy!