Recently I had five cars and two motorcycles titled, insured, and ready to use at any moment. I felt like it required nearly all of my free time to keep everything going.
What is the most cars that you have ever had going? Did you farm out any work/maintenance?
This summer, we peaked at seven cars at the house. Truck, Mini, Accord, E49, E39, Civic, and FSAE car. Back down to four now, which is much easier, although I still don't get to keep my car in the garage. 
Edit: This was in a two car garage with no off-driveway parking. It got a little crowded.
6 cars.
46 CJ2a
1986 CJ7
1986 CJ7
2000 Grand Cherokee
1976 Mini 1000
Seeing the mini parked side-by-side with one of my lifted and built CJs was funny.
3 cars and 2 bikes currently. I've had more in the stable but never had more running. Right now, everything I have actually runs and drives!
I do all my own work, and all the cars are older. It does take a lot of time to keep everything nice, but I'm starting to get to the point where it's tapering off. The trick is to keep things long enough to actually finish all the projects and only have to do routine maintenance, haha.
Three cars/trucks. Not too bad although the ex never understood why our checking account took such a big hit on "fill everything and change all the oil day".
two..but then, I rarely own more than that
5 currently registered plus with one unregistered
5 cars (318is, Milano, Elan, 9-3 Viggen, 325i convertible) 3 bikes (VFR750F, DRZ400s, TTR125LE)
Four running and licensed (Astro, MINI CooperS, Miata, Scion xB) and two more in the garage ( '91 GTI that's running, and '73 Corolla for the Challenge). I'd like to buy something for rallycross but SWMBO is acting up.
3 was the most I had at once. DD, challenge car, and my truck. That was expensive when you looked at plates and insurance.
Not counting the significant others Mazda, 4 seems to be my running limit. 2 cars, 1 bike, and a truck. There are still 2 I need to get running. And with a broken exhaust manifold on the race car. A brake job required on the dr. and the bike in winter hibernation I'm down to one right now.
I don't like it!
I've often had a half dozen licensed out of the 9 we usually keep. No time to use them all and the old ones can't be driven to work, so they get to share weekend time.
Including paperwork, only 2. I had 3 running at once before when my donor Corolla was running...barely.
we had 12 when I was a kid. 2 Mercedes 2 Audi 2 Buicks 1 Conv. Van 1 Austin Healy ! Jag Xk-120 2 MGA 1 Alfa Giulia Spider
I currently maintain 7
1 BMW 1 SAAB 1 Acura 1 CJ-2A and 1 of the old MGAs, the Jag and, the Alfa
Most i've personally had was 4 running, plated and insured at one time. And one of those was driven by my daughter in High School. Now "down" to 3 on the road with 2 project cars on hold.
For the past year and a half I've had 6 cars on the road, all of them getting regular (if not frequent) use. Dailies for me, SWMBO, DD#1, and DD#2, plus the Battle Bus for utility use and the Manic Miata for play. I have 7 cars, but the Poncho hasn't left the garage in a few years. That's probably changing soon.
Most was 13 at one time. Right now, 7 but one of them technically doesn't run. Its missing that big cast-iron thing that makes noise under the hood. But its registered and insured, so I could legally push it around on the road.
4 at present Two daily Hondas, my track wreck Civic, and Lamont the GMC Van, well technically 5 if you count the BIL's car which I both own and maintain. There are 3 VW's on the property 2 of which have a chance in Hades of running again one day. I think I need to thin the heard.
You guys are making me feel good. 3 cars and a bike currently and that is the most ever. Now there is also a old trailer and an old boat, but you said registered and insured...
I have always kept the number at three. My DD, DD for the wife, and hobby vehicle. That seems to be the magic number for me to keep everyone happy.
8, but they were all Italian, so it didn't last long! 
Currently I have three, the '11 370Z, '06 R53 Cooper S, and a new '15 RAV4 for the wife. The current "fleet" is actually pretty easy to keep running. I don't even know who I am anymore. 
2 BG mazdas, swmbo's sonata, DSM rallycar, 911, xB, 2 Volvo 240s, Miata, Titan and soon swmbos' 986.
Too many, The xB and DSM need to go, though I'll likely get a Frisbee once it does which won't help the situation much. A Cayman S would allow me to thin the herd a good bit more.
Five: Miata, Miata, '64 MGB, XJ, Slatern wagon.
Most running was four (including wife's).
Currently at two including the wife's. The 93 Civic is currently getting pulled apart before next autocross season.
Before I got married I had 3 cars and 3 motorcycles all registered and running. When we got married the wife added another 2 cars for a total of 8 vehicles. Shortly after her parents moved and we lost our storage place so we cut down to just 2 cars. After we bought a house we got back up to 5 vehicles (car, truck & 3 motorcycles) for a while. Currently we are down to 3 (2 cars & a truck).
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