I was making the equivalent of \~$80k in 2010 and owned an RX-7, RX-8, two square body suburbans (one for parts of course) a Cobalt SS, a square body Cummins and a rotating cast of project cars I'd flip on my time off.

How I pulled it off, my living expenses were hilariously small due to the broken economy and by luck my place had an excessive amount of parking. Used car prices were also hilariously cheap, in fact I pay more for rent now than I payed for most of the cars listed. The car flipping didn't add much to income, it was more to drive cool cars cheaply than profit at sale time. I was also single with no kids and young and stupid so I wasn't putting much of anything aside for the future.

Do I recommend it? No, absolutely not. For 1, good luck finding a place with 3 digit rent anywhere near well paying jobs, insurance costs have gone insane and it only made sense to me because I found an insurer that was willing to let me swap cars on and off the policy with a frequency that I don't think would be allowed today. Car prices have started to come down, but $5k is the new $1500 and even though I could easily afford what I was doing, much of that money should have gone to planning for the future.

Does your scenario make sense? I don't know, are you paying $1400 in rent or a $10k/mo mortgage? What's parking like where you live? etc. Here is what I can recommend, for a 3 car stable to have 1 economy, 1 utility and 1 fun car. Economy doesn't have to mean Prius (even though I dig the new ones), just something that's cheap enough to operate fuel and maintenance wise, for utility a mid to full size suv/truck is ideal but even a mini van can fill this role and for fun, well that's up to you.

In closing, I personally prefer multiple cheap cars over sinking all my cash into one nice rig. Since I could afford to do so, I have always had at least 2 vehicles that fill different niches.