Pumps were never a problem for me, as they were my first guns. The transition I'm struggling with now is going from a single selective trigger to double triggers.
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If you have a passion for upland and love the old stories of a simpler era a nice side by side is hard to beat. I have an a 1926 Ithaca 20 that I picked up a few years back for under $700 and brought back to life with some elbow grease and lots of tlc. Just got a Parker reproduction 28 gauge from the US, kind of a bucket wish. Sold a few guns and a aluminum boat to cover the price. lol One of the nicest guns I have used for upland is a Spanish Laurona 20gauge side by side--they show up every now and then go for about six to seven hundred --an extremely well balanced gun lovely to shoot.Attachment 40469 Ithaca 20 NID
I had a 20ga Ithaca Flues that I unfortunately sold before I had an appreciation of classic doubles. It was light as a wand and was interestingly choked IC and Full.
My next one will be a 20g double. I always watch the for sale section. It's hard for me to justify the price of new, I guess you never know what could come around.
My goto is a Rem Wingmaster, Special Field, 20 ga. 21" bbl. My second is the BPS Upland Special, 23" bbl.. Both removable chokes. Sorry, I am a pump guy.
Depending on where, and when I either use my 20 gauge Mossberg SRII, or my 20 gauge Mossberg SA-20. Choke depends on how much leaf cover there is, and possibility of longer shots.
I like using the O/U SRII, as if I'm in an area where there might be swamps / ponds, etc, I can open it quickly and drop a couple of 3" steel in for jump shooting ducks.
I shot the most grouse with a Mossberg 500 12 gauge, and next a Rem 870 20 gauge, but I think my favourite is a Winchester 1400 20 gauge, you just point it and they drop. Beautiful, light, well balanced gun with a nice chunk of wood to boot.