Jen,
I like the taildragger configuration personally, but I guess it is largely because that is pretty much all I know. I have only about 15 hours in tri gear out of just over 1000 hours.

Some of the plusses:

I prefer the look. There is something stately seeing an airplane with the prop up and tail down.

I like not having to worry about the most fragile part of the airplane when landing on relatively unimproved strips. A part, I might add that if damaged or destroyed can result in significant costs to any needed repairs.

Prop clearance was mentioned. I have a video of me doing some significant grass trimming once when landing at Fish Lake in Idaho. The grass was really tall - and I was tail wheel.

Some of the neutral issues:

Cross Winds - A flight of 6 - 5 Model IVs and one Nose wheel Rans S6, landed at Jackpot, NV. We were low on fuel and it was late in the day in direct cross winds that five of the six will say exceeded 20 kts. and the flight leader in the Rans (our bring along CFI) pegged at 28 kts. With some practice, cross winds are not much of an issue.

Feels the same in flight, but probably a bit less draggy than tri.

Recent posts tend to indicate there is not much change in CG with either - maybe a bit aft shift with tailwheel which could affect Baggage capacity some.

Negatives: Costly transition, as insurance for the first two or three years or so will more than double for similar coverage. http://www.teamkitfox.com/Forums/showthread.php?t=3968 That along with transition training can make it a real investment in cash for someone without the endorsement and some flight time. Jen, I suspect this will not apply to you as you mentioned you have been flying both ways for a while.

Visibility has been mentioned already, but I have gotten used to the regular S turns. My first Kitfox had a video camera on the lift strut with a viewer in the cockpit and I used that a lot in tight congestion.

One negative I didn't think of until I read John P's response. I have a hangar / shop attached to my house. I think I have more scars on my hairless head from trying to plow my head with the trailing edge of the flaperon than I would care to admit. There is almost always a scab on my head. I have seriously considered making an electrically winched ramp to lift the tailwheel for more clearance under the wing when indoors. A side benefit would be the better access to the engine compartment without needing a step stool. I definitely consider the greatest annoyance having to duck the wing every time I pass under it. Tri gear would definitely help in that area.

As John so well states it, it is a personal thing. Consider your mission and the numerous other little details.
Lowell