I'll say yes to starting with a Cajon with a wood playing surface first. Why? It's not that it would be wrong to use a fiberglass surface, but if this is your first Cajon ... it just seems right to get a traditional version first. That's just me and how I feel about it.
I feel the same way about Congas. I would want to own a set of wood congas first before I purchased a fiberglass set. I just want to have the traditional sound and feel at my disposal first ... then expand to accommodate my needs, such as having an instrument that will give me more volume.
My first Djembe was a traditional one, rope weave and all. Then I purchased a wood Djembe that was bolt tensioned. After that, I purchased another Djembe, fiberglass with bolt tension. Now I have multiples of the same instrument to choose from based on the sound I need or want.
All of this is just my opinion and personal tastes. If you feel that you want ONE Cajon in your arsenal, and really want the volume and durability that you will get with a fiberglass faced Cajon, go for it! I've not played one to say whether or not the difference is substantial enough to make it my first purchase (if I were in your shoes).