I know this is mostly a DIY forum, but...when you get a teardrop for $300, maybe you might be able to afford to get a workshop to do the epoxy fibreglass waterproofing?
If not, it probably is within your ability to epoxy it yourself. Here in Australia, we are not limited to woven fibreglass mat. We can get what is called CSM (chopped strand mat).
The whole point of that material is to follow complex curves. I would be very surprised if that isn't an off the shelf item in your neck of the woods.
Compared to making woven mat go around corners, it would be a piece of pie, I think.
Failing that, if you feel that it is beyond you, you could try what I did.
I thought I knew better than most and insisted on painting my teardrop with oil based gloss enamel paint. I am here to testify - oil based gloss does not flex enough. It cracks as the underlying timber swells and shrinks in the rain and humidity.
I had to find a remedy.
I found a paint-on acrylic membrane made for waterproofing timber decks and balconies.
It is kinda like the waterproofing membrane that goes in a bathroom before you lay the tile over the top of it. In fact, the one I bought said on the label that it could also be used for that purpose. I believe the thing that made it different to the usual bathroom treatment was this one was formulated for outdoor UV resistance. Anyway, it has worked. It doesn't dry very smooth, and it is opaque, so you lose the cool timber look, but it will be water proof.
I painted over mine with water-based house paint, as the membrane was a boring grey colour. If I'd used the right paint in the first place, I would not be telling this story.