I've done a bit of digital photography through my scopes using at first a little Nikon coolpix compact and more recently a Canon 1000D. The scopes have been a little 102mm f5 scope (available s/h for 80-100) and more recently a 200mm Schmidt-Cassegrain scope that's too heavy for a photographic tripod. There are plenty of nice little apochromatic or semi-apo scopes around that cost 200 to 300 and would be easy to use on a fairly beefy tripod. They'd work v nicely with a lightweight DSLR, I'd have thought. Makes like Williams Optics, Revelation, Skywatcher; not as expensive as birders' fave like Leica or Swarowski.
