Yes I have had several combo's that work well. I have a 1, 3 and 5 year old.

This was my first setup (Britax Marathon, Combi Coccoro, Safety 1st Complete Air:


That X was crashed so I got another X and new seats.

This combo worked but it was a tight squeeze to buckle the booster (sorry, you get my kids in the pic, I don't have a pic without the kids ) : Graco Turbo Booster, Combi Coccoro, Safety 1st Complete Air



Right now I have a rear-facing Combi Coccoro behind the driver's seat for my 18 month old, forward facing Radian XTSL in the middle for my 5 year old, and a rear-facing Radian behind the passenger for the 3 year old.

Honestly if the 5yo fits, a harnessed seat like the Radian is the way to go as it's narrower than most boosters and it's easier to buckle. A Radian for the oldest, with a narrow infant seat like the Combi Shuttle or Chicco Keyfit (or skip the infant seat and go for the Combi Coccoro) and a rear-facing convertible like the Radian or Complete Air would be perfect