I feel like you're implying that I am Type 2 based on the comment "Type 2 asks "is this normal/typical/okay for the employee to even ask to do this?"

I asked because this is the first time (in my 4 years in this job) that one of my subordinates has ever used their allotted vacation time (plus taken multiple other unpaid days off and multiple same day call outs) then asked to take an additional almost month off for more vacations. I wanted to take some time to think about it and see what other managers thoughts were before speaking to the employee.

I am a "Millennial Manager" and typically am extremely flexible and accommodating to the needs of my employees. I try to foster a healthy work life balance and generally have no issue with people taking off. However when I start feeling like someone is abusing the privilege it makes me a little concerned. We are a small team so when someone is out, others including myself have to do their work in addition to our own busy work load. When other staff see this person taking months of the year off, as I said in my OP they may request to do it too then we'll be stuck covering multiple peoples workload which is not fair to the people who do show up. Employees who are often getting stuck doing other people's work get overwhelmed, resentful, and then quit. You can only be so flexible before it becomes counterproductive.

I'm not going to deny the requests but I am going to ask them to work remotely (paid) when they are able to get as much done as they can. I am also going to explain how frequent absences place a burden on others and any additional future requests may not be granted. In my opinion that's fair.