OK, I have always been one to roll my tents. My reasons follow:

1. The wet bottom stays on the outside and the tent doesn't get any wetter (or drier) even in an all day rain
2. The dirt on the bottom doesn't contaminate the tent
3. My previous tents easily rolled up pretty small
4. It winds up being one compact package that carries nicely on the rack

So then I got a new tent (MSR Hubba Hubba) and find that it doesn't roll up into a tight small roll very easily. I am not sure if it is the material or something else about the design. Any way it got me to thinking about possibly using a compression sack. My concerns with that are:

1. Moisture on the bottom seems like it would get distributed to the whole tent
2. Dirt would seem likely to do likewise.
3. It would wind up being two bundles (poles and tent)

I am one to leave camp early, sometimes well before daylight, so letting everything dry in the mornings is not an option. Drying out during the day seem like an extra hassle that I'd like to avoid as much as possible. Drying out in the evening isn't always an option.

So my question is, how do those of you who use a compression sack or even just a stuff sack for the tent deal with those issues?

These days I typically just use my bivy when solo, but do sometimes use the tent when touring or backpacking with someone else.