One tip is to find an insurance company that allows moving cars into/out of storage insurance as needed. Farmers allows this 2x per 6 month period. My typical vehicle insurance costs goes from $1 per vehicle per day ($180 per term), to about $30 per term in storage. Not exact numbers but it significantly defrays the insurance costs for unused seasonal vehicles. My very handy reliable beater costs me about 50 cents daily fully insured, down to about 5 cents daily in storage insurance. Approximate numbers from cursory memory. I can work on the normal stuff, belts, fluids, etc. for practically nothing. In the 5 years I've had it, I doubt my entire total cost with ownership, insurance, maintenance, etc exceeds $3000.
I've had anywhere from 1 to 5 vehicles. It seems to me, as a single home owner in a small town, 3 is probably the most efficient and it's hard to justify more unless specific reasons. Having 1 is just too difficult and inefficient, you're stuck if it's being repaired, it's hard to have the "best tool" for the season/task, etc.
I think a truck or towing capable SUV (and a small trailer) is almost mandatory for the versatility and home improvements, DIY, furniture and appliance hauling, and so forth. Ideally 4x4. Something low valuable and reliable for winter months if you live in a northern state that salts roads; life span will be a decade before rusted our, or probably crashed into or otherwise just worn out. A winter beater should be AWD or FWD in my view. A nice weather daily, which can also dual as a fun car and something you spend most of your time in. So, yeah, 3 vehicles being a 1) truck frame, 2) beater/winter, and 3) daily/fun. Could possibly expand those into 4 categories I suppose, maybe a heirloom hand-me-down, maybe a track-car, or a work van, etc., or a classic truck or car, or some other special category that might not be so much a car but a parade-worthy vehicle, high sentimental value, etc..