Do you feel comfortable outsourcing your IT or do you prefer to keep it in-house?

Do things that are your core competency, outsource that others have competency on!

Like the others, my answer is "it depends." Managed Service Providers are good at providing "average services" if you have a function that needs to be above average in your organization, it may need to be delivered by an in-house team.

It depends on the complexity and sensitivity of data

It is a balance between outsourcing the basic operations like deskside support, network management etc. and retaining the business facing and consumer facing roles internal.

I don’t feel it should be 100% of either. The right ratio depends on the business, where it is in maturity and growth