Family of 4 and I'm starting from scratch.

Needs/Use:
-Kids are 2 and 5 (3/6 later this summer)
-Riding will be contained to street, bikepaths, riverwalk etc. No serious terrain, but more than riding around neighborhood block.

My Initial Thougts:
- Hybrid/Cross for wife & myself
- Trailer for 2 year old
- Tag along for 5/6 year old
- Vehicle Rack (for Odyssesy)

Budget:
- ~1200 for the 2 bikes (new, not bent on spending 1200, that's max)
- ~ 200 for trailer (will try to go used)
- ~200 for tag along (used or new
- Vehicle Rack ~500

Ok, so those are my thoughts but I'd like some advice.

Bikes for Wife & I --For the use described, if I want a mix of comfort and agility from a bike should I be looking at hybrid/cross or? Wife and I have had mountain bikes in the past and I'm beyond my days of heavy terrain with 2 and 5 year old. I want narrower tires for quicker cruising, but the ability to go off road a little if needed. What brands/models, would you suggest checking out? Am i going to get that much more bike out of a $600 as opposed to $400? Want to have these last at least 5 years without dying to upgrade.

Trailer- Was thinking about going used Burley D'Lite. See lots of recommendations for Chariot on here, but haven't seen many used in the midwest. Is Burley Good enough?

Tag Along- Totally clueless here. What brand, model and price range do I need to be looking at? Figure getting a year or 2 out of it from 5 year old and then transitioning my son into it when he's old enough.

Car Carrier - Have a Honda Odyssey. Want to avoid the roof because it seems like a pain going up so high. What's the best brands/types for back of the car. Figure I'll have to get a low grade hitch and then mount the carrier to it. Want something that folds down or to the side so that I can open the back without taking the hitch off. No idea here, any suggestions on what to do and dollars that need to be spent for something that is sturdy and will last awhile would be appreciated.

Appreciate any insight. Thanks