Seems like many here have had great experiences (luck?) with their older cars. Just to give other side of things- 2 not-so-lucky stories from close Midwest relatives:
1. Bought used 4yr old mid-size sedan from trusted neighbor who bought it new & kept meticulous care of it with all maint records. Paid only ~$10k for this cream puff w/35k mi (preferred to sell to friend vs dealer @ trade-in value) . Car ran perfect for 18mo, then over next 18-20mo (35+k miles) needed pwr window fixed ($250), new brakes/rotors ($750), timing belt (scheduled @ 60k mi, $1100 inc water pump as it's little extra labor during TB replacement), & new tires ($600). Then tranny went (~71k mi) costing $2950 for rebuild. So almost $6k in maint + repairs plus ~$5k in (private sale-not trade-in) depreciation, or ~$11k ($3,667/yr) for bit over 3yrs/36k mi for a 4-7yr old sedan.
2. 3yr old mid-size SUV w/37k mi. Over same 3yr period- brake pads/rotors ($825), timing belt ($775, sched maint @60k), 4wd system repair ($875), and tires ($625). So 'only' $3,100 in repairs/maint but also another $9k depreciation so $12k ($4k/yr) for again 3+yr/37-38k mi.
IMHO- Annual depreciation is still surprisingly significant for 3-4yr old vehicle (unless you keep it many yrs), and many folks do not have a great repair expense experience. So for scenario of buying 3-4yr old vehicle & driving for ~3yrs, overall costs can be surprisingly similar to some better corp lease deals. Examples from recent national/regional (US mainland) car maker (NOT dealer) web ads: Total costs (mo pmts + downpmt + acquisition/disposal fee) for 3yr/36k mi lease specials included ~$8100 for Toyota Corolla sedan and ~$11k for Honda CRV SUV.
For car guys like JoeWras, I tend to agree that buying new & running for dozen yrs is prob perhaps best way to go.
And I think leftbucket's scheme can work too, although maint/repairs on luxury cars can be more expensive than for more common vehicles.
DISCLAIMER- I am not employed in auto industry, take good care of my rides, & tend to prefer mid-range vehicles. My last 3 vehicles were a 3yr lease, new purchase kept 9 yrs, and new purchase kept 4 yrs.