Between The Dude and this, SS is clearly looking at deeper cut licenses with smaller but passionate fan bases. So maybe they are looking at shorter runs and better quality artisanship which will enable them to charge higher prices. To be honest, neither license is that big of a priority for me. I wouldn't pay $200 or even $150 for a pretty good The Dude or Dirty Harry figure. However, I would pay $300, possibly $350, for great figures.
There are some amazing Dude customs out there so that bar is set pretty high. That said, since those customs are unlicensed Sideshow could conceivably work with one of those artists to try and mass produce a figure that can rival the custom. I've also seen nice Walter Sobchak and Jesus Q customs if SS wants to expand the BL line. As for Eastwood, I believe Scott Pettersen did a pretty nice Dirty Harry a few years ago. I have the Iminime Blondie, which is good but can certainly be topped. Again, Sideshow could work with those guys on outfits and hire a top sculptor for the portraits. They could also produce Tuco and Angel Eyes to round out the GBU cast.
But with Sideshow who knows. They were able to raise the bar on their statues when XM came on the scene, but haven't come anywhere close to Hot Toys in the figure arena. That's probably why they lost the 1:6 Star Wars license (although they've never acknowledged it publically). While they are producing 1:6 Marvel and DC comic figures, those are underwhelming and inconsistent IMO. The last 1:6 figure I bought from SS was Jack Burton, which was okay but not great. I would have ordered Beetlejuice had it not been so terrible. But again I would have paid up to $350 for "custom" quality figures.
I guess we'll see where they go.