Car Seat, Stroller, Travel System?

Jenna
I'm working on my registry and I'm SO overwhelmed! I'm a FTM and we're expecting a boy, but hoping to have more kids down the line, so going for gender-neutral colors. I like the Chicco Keyfit 30 car seat for the safety aspect, but not loving the price of the travel systems - $300ish is my goal. Does anyone have (and love) the Graco Aire3 system? Or would you suggest NOT doing a travel system and getting the car seat and stroller separately? Hubby and I like the idea of a 3-wheeled stroller for ease of use in our city, but open to 4-wheeled options if you really love them and they're easy to use. 
Thank you SO much for your opinions - I can't believe how much I'm stressing over this but I just want to make the safest, best choice for my little guy!