A couple of thoughts. It’s already been brought up, but do you really know what you are looking at used? I know how it works, after you own something for a while you learn the quirks and problem areas.
I always look at something from a cost per use or in the case of equipment per hour. A strange example, a bicycle. I was unsure about buying a $500 Trek bicycle years ago. If I road it twice and let it sit, that was $250 a ride, a bad purchase. I have probably rode it several hundred times so it’s maybe only $1 a ride now, a good purchase.
I have actually sat down and estimated my last tractor cost per hour, a Kubota BX. I tried to figure everything, residual value, fuel, maintain etc. it’s probably a little less than $15 per hour. So if it takes me an hour and a half to mow, could I hire it done for $25? Not even close.
So if you buy a mini exec for $20k, work it for a couple of years and sell it for 20k, you probably just had a few dollars an hour in it for fuel and maintenance. On the other hand you buy one with problems, spend 10k on fixing it, don’t use it much, you could have several hundred dollars per hour to use it, a bad purchase.
My point is can you get a good buy, not have to put a bunch of money in it, and sell it for near what you paid? The safe thing is to rent, but that may or may not be the correct answer. There will always be people that buy cheap and sell high but are you that person?