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In the Option 1 case, what happens when you finally have to "hire someone with more experience/knowledge"?

My first thoughts as well. Hiring in someone else over the top of a key hire can be problematic from a cultural standpoint.

Thanks. This is my concern as well. It would be bad to push someone away who has been there for awhile... Any solution to this if I go with #1?

If everyone is still wearing lots of hats, get a CTO and put IT on his plate. He can hire the sysadmin later at an appropriate point.

However, I am pretty much assuming CTO equity is in the offer.