Been sorting through the same dilemma myself. Currently have 6 cars and 5 bikes, which is too many. Bikes are less of a problem, but it all adds up to lots of time in the garage and less time doing stuff.
1. 1991 318is turbo. Blown engine, has been for 2 years. Have all the parts but none of the time. Was my first car, love driving it, it's not going anywhere. Great track day and nice weather car, and passable for longer trips without luggage since turbo + muffler kept it pretty quiet.
2. 1998 Silverado K1500. Good for truck stuff, have driven it across the country as a race bike rig a few times. Boring. Caprice wagon in the background was sold when I bought the Tahoe.
3. 2000 Chevy Tahoe Limited. Wanted to see if an SUV would make a better race bike/cross country trip/trailer hauler than the truck and still have some daily driver fun factor from the Caprice. 2wd with the G80 locker and simple as a box of rocks, and surprisingly good mileage. I have a T56 6 speed to swap in, and an engine with more juice, but it's so good right now that I'm not in any hurry. It's almost shockingly fun to drive with the chassis updates, and being able to lock stuff inside and sleep in the back makes it all-around more useful than the Silverado.
4. 1984 Porsche 944 LS1 that I bought from a member here. Ongoing long term project car, with time trial goals. Slow progress since focusing more on bike racing.
5. 1986 Porsche 951. Runs and drives but was rear ended, so parting out and keeping some parts for the LS1 build. Surprisingly no pictures of this one.
6. 1987 BMW 325is 5 speed. Runs and drives well but major rust. Fell into my lap and couldn't say no. Either going to buy a good shell and build a nice-ish E30 to flip, or will part it out. Undecided yet, and until then will probably use it as a daily driver. No pics of this one either.
The 951 is obviously not long for my garage. The 325is probably isn't either. But I keep coming back to what to do with the other four. The E30 is a keeper. I have to finish the LS1 944 before I can make a decision on it, but I think it will be a better and more reliable track car than the E30 considering some of the repeat issues I have with the turbo setup. But right now, I'm not spending nearly as much time at the track as I thought I would be since discovering my love of dirt bike stuff.
Do I keep the Tahoe and the Silverado? It's kind of nice having a truck with an automatic sometimes, and 4wd can be useful. Truck stuff obviously is easier with a truck. But simplifying to 3 cars does sound good and the Tahoe has already proven to be a better all-around vehicle. Until the Silverado, I had never had 4wd before anyway.
for now, the bikes aren't in question. They all serve a different purpose, are much less of a time and money sink to have around, and all get used more than most of my cars.