The fact is, you have unreasonable expectations regarding life expectancy of computers. 12 years old is old. Heck even XP is 8 years old and is showing its age.
Who made you the authority to decide what is reasonable? GP is right - it is more user-friendly to provide support longer term than what Apple provides.
GP makes a great point.
"Remotely" doesn't mean offshore. All big outsourcers - especially those who have large offshore operations - make their offshore staff sign all sorts of confidentiality and privacy contracts. A sysadmin in India is as likely to wind up in jail as a sysadmin here. A worker in a Chinese factory committed suicide just because an Apple prototype got stolen from him.
In addition, outsourcing contracts have liability clauses for breaches. So get the vendor company to agree to liability clauses and protect yourself.
Any web developer worth his salt ought to have strong experience with the UNIX shell, shell scripting, and Apache configuration. Developers with broader interests should have Photoshop, Illustrator, and Flash at their disposal. And every developer should have decent C/C++ skills.
And he should be able to dance, cook, be good in bed, know how to sail a boat, be good with kids and impress my parents.
WTF?? I could climb Mt. Everest but not your ego.
Have you ever watched TV in other countries? If it's not reruns of old stuff from the US, It's knock-offs like [insert country here] Idol. Entertainment is bad on a global scale.
Before you take too much misplaced patriotic pride in the silliness of American Idol, you should know that it's a ripoff from a British show. But it's too late for that I guess.
A good supervisor can step on your toes without messing up your shine.