You must look at your purchases as an investment. By Quality and bikes that FIT. I can't stress that enough. Most entry level LBS bikes will do fine for you and your wife for now, but... what about later?
On the Cypress. Not a bad bike, but a 19 is going to be on the small side for you. The bike I built up for myself this year is a 21 inch frame and there are times that feels small, and I am only 5'11".
The Trailer is going to be the pricey part of this deal unless you can find a "GOOD" used one. If you go used, look for a Burley or a Trek so you can get replacement parts easier. Look to your Craiglist for deals and look multiple times a day. This are items that move fast.
Good Luck