You need to decide on the access the person needs when they are hired. If you are getting a system administrator, then make sure you can trust them from the beginning. Even if you figure out a way to prevent any one individual from being the sole point root admin on your system, you still have a brilliant person well versed in how that security is set up that can still subvert it. The key is to trust your root admins and hope they are doing the right thing; the other option is to not trust them, which will cause stress and animosity, and they'll probably still figure out a way to burn you even with "safe guards" in place.

Wow, that type of longevity is very ambitious. If its just hardware he wants upgraded, then go for it. If its software, then leave it to the pros because there are plenty of canned office management suites out there. Yes they are expensive, but you know that if you install, then the next 10-15 years, you will be the tech support!

It is in their best interest to just stop the money because customers won't pay their credit card bill for bad software. For example, my CitiCard does not work for bodoglive and I called citicard about it. They told me they don't allow payments to them because customers stiff them when they are done gambling and just say bodoglive fraudulently changed their card. The credit card companies should be stopping payments to these companies or at least putting a hold on the card and contacting the customer for confirmation.