UPDATE: Missed out on that one, so going to look for a decent shooter grade while getting fun gun funds rebuilt.  Single Six still has a home.  

UPDATE 2:  Won a shooter Pre-Woodsman at a great price and have a healthy stock of CCI standard velocity, which I'll continue to add to, so I'm set.  All firearms are safe and sound, and no plans to sell any in the future.  Sleep easy, and thanks for the thoughts, all.

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Reader's Digest version:

My grandpa had a Colt Woodsman that went to my cousin when he died.   To me, the Woodsman has always been number one on my bucket list.  

I have a Lipsey's 4 5/8" stainless Single Six with both cylinders that I've used as a field gun for a few years.  It's set up with Williams sights, a Simply Rugged Sourdough Pancake holster, and a healthy stash of 22mag and other 22.  It's very practical and been a great gun, but I'm the only one in my family who likes to shoot it, and these days I pretty much only carry a 10mm as a woods gun anyways.

I have the funds, but have blown my current fun gun/hobby wad (and then a little bit) and wasn't planning on any more gun purchases until next year.  

I found a great deal on a very good condition series one Colt Woodsman made the year my dad was born.  I can buy it if I sell my Single Six, which my family doesn't enjoy shooting as much as I do.   I always preferred shooting Grandpa's Woodsman over the Single Six.

I can wait until I rebuild my gun fund and not have to sell the Single Six, but this Colt and deal will be long gone.  My family will enjoy shooting any semi-auto .22 over the SS, but the Woodsman has a special place in my heart and they've been getting pretty damn expensive, so this deal is pretty attractive.

I have a family heirloom woodsman, I am very, very happy to have it.

Get the woodsman , you can always easily replace a current production Ruger when cash flow improves.

I bought a Woodsman last year, then picked up a Buckmark. I liked the woodsman but the buckmark is far better for me.
Ymmv.

I'm keeping both of course, cause I've always regretted selling, it's bad karma!

Thanks, all!  Until the two party poopers in the poll (j/k) it was 100%, which I didn't expect, so I took that as a sign from the cosmos.

I missed my shot at that pistol - I was winning the auction but took my daughter for a walk on the beach and got outbid before the auction ended.  Made me physically ill to come back and see it went.  I should have put in $100 more than I wanted just to seal the deal.  

That said, I'm currently winning an auction a pre-war Woodsman from the same year with bluing in even better condition.  One grip panel has a small stain that can be gently treated out, but it's otherwise good to go, and the price is very low for the condition. We'll see soon, but either way I'm determined to get a Woodsman and at least one correct spare mag in the very near term.

I've got no hangups over selling to buy, which I've done for decades.  Of all of them, I only feel bad about one beautiful 1945 Springfield M1 Garand that I sold with 2K+ of Greek ammo in spam cans, but that and two Stewart longboards paid for a good chunk of my wedding, so I still can't say I regret it.  (But I do secretly, deep down inside, despite a beautiful wedding and being happily married years later)

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Snipped. Was thinking out loud, not trying to sell anything.  Thanks for the IM offers, but no thanks.

Selling something useful for cash to spend for a unsupported by the ex-factory collectable is silly.

Buying at 100% $ and then selling at 60-80% $ is how you go broke and end up with junk.

Buy AND keep guns.  Buy wisely and never sell any part of your good judgment.

Yes.  What's wrong is fantasy land auction interest.

Your daughter on the beach is far far more important than a fantasy about a gun sorta like some dead relatives.  

Auctions and bidding become an addiction leading to no money.  Few relatives shooting your gun give a damn what it is as long as you have ammo and it goes bang.

Distinguish need/use from an itch to be a "player."  Guys with no money should spend it on the kid, not on guns.

There’s no doubt I enjoy my daughter more than anything else, and would rather walk on the beach with her than win anything.  Of course, if I could walk on the beach with her AND win a very good condition complete Woodsman for $450, I’ll take that.   I haven't used GB in 10 years, so I'm not in much danger of succumbing to addiction. I'm a teacher and scientist with no aspirations to become a business tycoon, so I will never have a bottomless recreation budget.  I’ll be sure not to spend my kid’s milk money on a symbolic wangdoodle.  

As I said before, this is one gun I've wanted for decades and don't have that has a greater nostalgic value to me than any other firearm I could own.  I haven't used GB in 10 years, so I'm not in much danger of succumbing to addiction, and I'm not going to buy a $1,800 Woodsman in the hopes of completing myself, but if I can find a deal that doesn't break the bank for a shooter-grade...  I'm not into amassing a collection of guns that I don't care to shoot, dragging them through the rest of my life like anchors that I have to buy more bedrooms for.  

In distinguishing between need and want, if the value of one would cover the other, I'd rather have and use the Woodsman, which would out perform the Single Six in speed, accuracy, ease of use, and sentimental value, to me.  

Kool.  Completely understood.