Right now the family fleet is as follows:
Daily Drivers:
1) Jeep Liberty (Main family vehicle) -- 'Poser Jeep' bought for SNOW and basic transportation. (If we wanted to off road, we'd build a CJ)
2) Ram 1500 (Company vehicle)
3) My Mustang GT 'vert. (My daily for a year now)
4) The GF's Cav (Usually does a lot of sitting as we prefer to drive the Stang. That might change in light of gas prices tho)
'Fun' Cars:
1) 68 Camaro (Was used as a semi daily driver at one time)
2) 73 Camaro (Was my daily driver for 4-5 years at one point)
3) 99 Silverado (Replaced by the Jeep as a daily; now is only used for 'truck' duties mostly, but not any 'cowboying' like off roading)
4) 82 Toyota Starlet (Was a daily driver; retired to third car status, came back as a daily driver; now has been retired again and might actually get 'scrapped' soon)
4 people, 2 houses, 8 cars (not counting the 76 Dodge Power Wagon that my GF is trying to inherit from her parents)
I ALWAYS see myself owning many, many cars. In fact, there is a 73 Jeep Commando up the street which a friend of mine just purchased that I would've bought in a heartbeat if I had the extra $$$. $1800 for what is basically a fully restored Jeep.
I'm not so sure I see myself ever owning anything new again; 1) Because it's a horrible financial decision 2) Because I want to collect old cars and 3) Because my needs are too diverse to consolidate into one specific car. Next purchase will probably be either a people mover of some sort to replace the Cav (HHR SS or some small ute) or something to either replace (the stang) or supplement the pony cars (new gen GTO or G8, 67-68 Firebird, late 50's early 60's Buick or Caddy. Or maybe even something truck or 4X4 like an old International or Bronco or a 40's-60's or 90's GM truck -- We have to have something to pull the cars and the vintage Airstream we're going to buy )