So here are a few strollers that I have been looking at - if you or someone you know has any recommendations please let me know!
Here are the contenders so far.
First up Baby Jogger's City Mini Double -
Slightly pricey. Quickly folds down to almost flat. Has an adapter for an infant seat. Side-by-side which will make shopping challenging. Great canopies for outdoor activity. Wheels more suited for various terrains.
Next up Chicco Trevi Twin Stroller.
Folds very compactly. Seats recline fully. Lightweight. Comes in a variety of cute colors. Gets really good reviews (as do the other two).
Finally - Baby Trend Sit n Stand
Accommodates infant seat. Only one with a snack tray for child on front. Lightweight. Not sure if Ryan will be ready for a bench seat with seat belt or if he will still want to relax in the stroller from time to time. Not sure how it will hold up on neighborhood walks and off-road type conditions.