Any recommendations?

Merkel or Simpson; I have had both. The Merkel was heavier and has a blitz-type safety that when pushed forward beyond fire cocks the rifle barrel. The barrel is decocked when the safety is returned to the middle position or to safe. The advantage is one button for safety and barrel selector on the top of the tang. The Simpson is lighter weight and has the selector in front of the safety, but also on the top of the tang. I sold the Merkel to buy the Simson. You might also consider 7x65R; basically a rimmed .280 Remington. I have had the 8x57R and the 7x65R, and have not determined that there is any practical difference in the game they are suitable for. My Simson is a 16-gauge/7x65R, weighs just over 7 pounds without the scope, and handles like a good shotgun. I have a fixed 4X Leupold scope on it in a swing mount.

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Simson
Sauer & Sohn
Krieghoff
Merkel
Hunold Halle
Carl Hauptmann
Franz Sodia
Boehler

and so many more! Scrolling the German and Austrian gun sites you are (or maybe we are) spoiled for choice.
Working, good condition Drillings starting at EUR 500/- up into the thousands of EURs.
Most 20s and 16s with a few 12s and then many / any rifle calibers but lots in 8x57 and 7x65.
Frequent barrel inserts /ESL in .22s.

Looking at some of the larger sites, the most common Drillings out there for sale seem to be the wide range of Krieghoffs - Neptun, Trumpf, Plus. A nice Trumpf for sale at moment in 7x65 - 16/70 with a Zeiss and a Schmidt & Bender glass at EUR 2.700/-

I sat my German hunting exams a decade ago plus some, and Drillings featured heavily then in the exams and also the stores. Learned all about them then. I never did become a fan of the Drilling as I saw it as a jack of all trades for the high seat hunter ( in Germany ) who would go out and potentially shoot anything that would come by - fox, hare, badger with the .22, roe, boar or red deer with the 7x65R and pigeon, hare, rabbit with the 20 or 16 bore. Whereas I believed you went out with one quarry in mind and targeted that quarry with either a rifle or a shotgun in the appropriate caliber and if you were after roe then don't shot hare or rabbit or a badger should they come strolling by. But that was just my opinion at the time.

I have a lot of guns today, too many perhaps, but have not brought a Drilling yet. If I did, I think I would go for something from the Suhl block and try and find mid 1960s or early 1970s with some classic German engraving - roe, red, boar, gams, fox and the likes. But that's just me speculating!

If I were to look for 'something newer', I wouldn't overlook Krieghoff - some great Drillings there to be had for sensible money. Well, in Europe at least. I have no idea what the market for Drillings in the USA is like.

Not hijacking your thread, just putting a European 2 cents into it if I may..

Good luck in your search!

Charlie

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I have 3 Sauer 3000 post war, made in West Germany drillings. They have been trouble free. Whichever you choose be sure to find one with quality optics and mounts already set up.
My best.
mike