Eons ago, my husband and I bought bikes and we used to ride. I LOVED it. However, we lived in Chicago, not the burbs, but IN Chicago -we lived just off the tip of Lake Shore Drive and we could anywhere so easily. We would ride to get coffee, to a bookstore - it was great, but it was EASY because Chicago is flat, flat, flat.
Then we moved to Philadelphia, well, whoa! HILLS! I had a little one then and we got a bike carrier, really, the only place we could ride was in a park that was fairly nearby and was flat (along a river). We did that sometimes, but it's a chore to load up a couple of bikes and a bike carrier.
Skip about a decade, we got rid of the bikes, never road as we were too busy and lived in a tiny townhouse that couldn't store bikes (except the kid bikes).
That was then. This is now. We now have a 14 year old, a 5 year old with high functioning autism and the two of us. I picked up this bike last fall: http://buddybike.com/SpecsBB102-AL-8.html My husband plans to pick up a bike as well. My teen already has one.
While this is all great, this buddybike is not a bike I can take anywhere easily to ride on flat areas. I would like to just ride with my 5 year old locally. We live in a planned community and everything is like RIGHT HERE. We are a mile from the mall, a bit over a mile from the library, the gyms, the pools, etc. BUT, it's hilly. I tried last year when I was super unfit to just go around our little island in the cul-de-sac and I couldn't do it because of the hill!
So, how does one get to riding in hilly areas when they are so foreign to riding PERIOD? I am exercising and trying to get more fit, but will taht translate well to riding a bike? I'm walking, mostly.
Add to that, this buddy bike is a bit upright - meaning the pedals are more under me than they would be on a regular bike, so it feels a bit odd. I could start going solo on my son's bike (the teenagers - as it's actually my size - he's probably getting too big for it). And then build up to riding this monster buddy bike?
Any bike riders out there with some tips on how to jump in successfully without having to walk the bike up every hill I encounter?

In all seriousness, that's probably the best thing because it builds up all the right muscles. You can buy spin shoes that clip into the pedals, something you can use on a regular bike too if you buy the special pedals, but frankly it scares me not to be able to unclip fast enough. I could stand on a bike as a kid, but I find it difficult now as an adult. 
But persistence and practice to build stamina will be the best. I hope you'll have some great photos and comments to share on your Buddy Bike some day! Take care!