Swampgatr, Consider what was suggested by RT above. For some, sitting in the marina would be reason to Not want to be on a boat at all. For some the marina would be the only reason to be on a boat. For most of the boat owners we know cruising out seeing the sun rise/set from a great anchorage, the incredible night sky away from the light pollution of the cities is what brings the good feelings of freedom, solitude and comfort to their lives. The adventure of new places new people to share stories with is so much more fun than the same old dock mates every day. You will do what you think is best for your situation and family.
On the thought of a 36 to see if you all will like it may be false experience if you really intend to go to 48. Just a thought. Don't "shoot yourself in the foot" so to speak.
Footnote we started Cruising with a 28 foot carver and loved for 5 years. Started shopping after the first year and in doing so learned what WE would need to increase comfort and fun. We shopped for about 4 years then found what we learned we wanted. HAPPY, HAPPY, HAPPY.
Welcome Aboard and good luck with your plans.
Toolbuddie.