There is always somebody with a 6 year old story of woe with the MacOS that feels it is somehow applicable to the modern operating system and hardware
The news flash is that there is very little difference in price anymore, nor in software or hardware availability either.
The difference is in the usability of the OS for those that care to take the time to fine it out. He wouldn't have asked the question if he wasn't curious.
I think we've covered that pretty good. If you want more stories of woe I'll tell you my 6 year old windows migration stories which are equally bad
If you dont care to experiment that is fine, I dont mind, really I dont
But the hardware and software that he'd be getting today would be new and nearly identical in price and speed to the windows counter parts. The differences now are not in price or availability, but in how you go about doing things in the OS. It's different in what I consider to be good ways.
You will always be able to find a stripped down windows box cheaper. You can buy the parts and put them together and probably shave $200 or so off the price of a new mac-mini for similar specs. And if this is something you're up for doing then more power to you! If it were me I'd run Linux on it and not windows though
Oh wait, I have one just like that under my desk right now running linux as I'm start to do cross platform development for linux and MacOS now. That is exciting stuff...
You can usually find pirate versions of windows software easier than pirate versions of Mac software too. If you want to upgrade to the next MacOS version 18 months from when you buy your machine,you're going to have to pay for the upgrade and not just download it and steal it. You're going to have to pay for Office if you need it and not just steal it. This is a big deal actually as a not insignificant percentage of people I talk to budget nothing for software in their computer decisions because they can steal anything for windows they want!
Oh, and I'm typing this on my mac powerbook sitting in a barnes & nobel using their wireless internet connection. I'm not locked out of anything by my choice to use a mac. I really have given up telling people what to do, all i do is share my experiences which as a cross platform developer who is always called upon to support his parents and friends machines covers most versions of windows and MacOS pretty well.
If you're curious enough to take the time to give it a try, you wont be unhappy with the decision.
This is all pretty general stuff, if I can answer specific application or OS questions, please post them and I will. There is a pretty large population of Mac users here on CPF, i'm sure we can figure out anything you'd like to know.