Brantel, in your shoes I'd start by looking at the location of "your wife's room" <s> as you'll likely want the easiest commute. If you are to the N, NW or W of the downtown area, Herlong would make the most sense (the commute thru downtown Jax and out to 9A/275 is very quick outside of rush hour if you use the one-way streets in Jax in both directions). I sure agree with the comments above about Herlong. Just remember: if landing there, you two have an obligation to somehow find the time for a game of pool as the FBO has had that tradition long enough that they built the whole new FBO facility around the dang pool room. Going there, in our experience, is like visiting family.
Craig is busy but of course on the S side of the city and the river, so if your room is over there (and it probably is), Craig would probably be preferable. Consider the car run to St.Aug in one direction using 9A and I-95 but the other using A1A or US 1 as it's a different experience altogether.
My impression is that going to Craig is like going to the big city, while going to Herlong is dropping in at a 1940's airport with 21st century facilities. Like cheese and chalk, the two are the same but very different.
Jack