When should you consider outsourcing?
If your company only has a few computers and a simple network, you can probably use the person in your neighborhood who’ll do it for a few beers or a gift card to Olive Garden. The company that sold you the computers probably even has some kind of support service, which you probably bought when you bought the equipment. But if your company has a website, if you have more advanced security concerns, or if your network is spread over multiple sites, then you should be looking for a vendor who has experience working with the types of systems.
The key things to remember about your relationship with your IT remote helpdesk provider are that a) they didn't break whatever it is that's broken; b) they can only work with what they can see and what you tell them; c) there are limits governing how much help they can provide, and they were put in place by you.
You should look out for a provider that speaks your language, and has experience of supporting your kind of business.
Weigh the cost of lost production or revenue against the cost of the support contract to keep things running. Consider it insurance—it will feel like a waste of money until something catastrophic happens.
Remote support is almost always a tiered system. Which is to say that you get a little help for free, which is fine if you're a network engineer, but let's assume that you're not a computer genius. The next layer of support will be, most likely, on a premium phone number. You'll probably get your computer back in action, but it will take your time on the phone, and the call will be expensive.
Your printer isn't working. Again. But it's just you. Nobody else is having a problem. You've done everything that you know to do, but all that did was make the printer angry and spit out pages full of little squares and symbols. This is where you step away from the technology and let an expert help you.