Hi Meg,
I'm not sure how much help I can offer given that my only experience is with Gaco on vinyl which is what my yurt cover is made from. If you could describe the "Test kit" and how it didn't adhere well to your fabric, I might be able to help more. However, what I'm reading thus far makes me quite nervous. I personally would not want to go to the effort with something that doesn't adhere well to your particular fabric. Going to the effort now to test various paints to find one that sticks well will save you a huge amount of time, headaches, and money in the future....and perhaps the not so distant future. I'm sorry to say that as I'm sure it's not what you wanted to hear, but....
That said, perhaps the Gaco sticks "well enough" that you can make it work. I'll just need to have you tell me more.
Re painting when the cover is off or on: That is something I debated greatly. I am really, and I mean really glad I did it while off....for a number of reasons. One being that I think it's much easier to get good coverage while the cover is laying flat. Two, the silicone paint will run and drip all over the place making one heck of a mess that would have taken me a lot more elbow grease (time) to clean up...with more nasty chemicals...and I probably wouldn't have been able to get it all. The Gaco is made for near horizontal surfaces, I believe.
I wouldn't worry it sticking to itself. Part of mine did....but it was the part that dried the least amount of time before rolling. Had I let it dry, I'm confident it wouldn't have stuck....but I was using a buddies shop and he needed his work space back.
Re cold temps, that's something else not to worry about with silicone. With other non-silicone elastomeric paints, it is an issue. Not with silicone. It'll dry when it's cold...it just takes longer. I touched up the spots in freezing temps after the cover was on.....where the cover had stuck to itself and peeled the silicone off. That was last fall. Those areas wintered and summered just the same as the rest of the cover did.
If the silicone isn't right for your cover, perhaps you could return the bucket you didn't open....and find a paint that adheres better. Of course, it would almost certainly be a paint that needed to be applied in warmer temps, in which case you'd need to find a heated shop big enough to paint it in...or wait till spring. If the shop wasn't big enough, you can fold part of the cover over on itself, paint the exposed part, let dry, unfold, then paint the other part.
Hope I didn't take too much wind out of your sail as I can certainly sympathize with what you're doing and up against.
Re the wool
, I don't know. Would have rather used that myself...but I also used a reflective bubble wrap....two 1/4" layers on the roof.
FN