Sounds to me like you have been around the block per say. You've tried this, and you've tried that, and now it sounds like you know what you really like. Sounds like you have a fabulous collection as I can imagine it must be fairly difficult to get some of the boots you have mentioned.
I on the other hand haven't been buying nice shoes or boots for very long so I'm still trying a bit of this and a bit of that. I have a couple I really like but they are all new and I have yet to be bitten by the vintage boot or shoe bug, but who knows where my journey will take me. When I bought my first really nice watch I had no idea I would eventually buy a vintage watch one day, but I did. I'm enjoying this part of the journey for now however as it's kind of nice going through the process itself of discovering what's all out there and what style or styles I like.
The shearling option is something I have given some consideration to, however with a another Galway, a Carmina cordovan jumper, and a suede chukka on the way it will probably be a little while before I look for my next boot.
If you ever decide to take a collection photo, I'd certainly be interested at taking a look at your collection.
Think it takes a while to find what works for you and what doesn't. Certainly, I don't need much in the way of formal shoes as that would just be over-dressing for work which is business casual and even wearing a welted shoe is out of the ordinary. I don't think calf oxfords really work with anything other than suits, so I might admire some of the shoes on here but I wouldn't wear them.
Some people find that the thought of wearing vintage stuff leaves them cold, and that's fine with me. The good thing about buying vintage is that it's generally relatively inexpensive, so a good way of finding what works for you and what doesn't. Also, most people selling vintage don't know what they're selling so it can be very easy to just flip the stuff that doesn't work for you at a healthy profit, which funds the next couple of pairs.
I've taken some pics of my whole, now-streamlined, collection tonight and in the absence of anywhere else to post them have hidden them in the spoiler below with an on-topic rehash of some recent Galway porn. Apologies to everyone else for the diversion!
The Edward Green 'Galway' pic (from left): almond country calf; mink suede, walnut country calf and shearling lining; rosewood country calf (made on 64 F last for Holland & Holland)
Warning: Spoiler! (Click to show)
The Tricker's pic (from left): unknown model of navvy boot, possibly 1950s; high-leg brogue boot predecessor to the 'Malton'; MTO 'Eaton', semi-brogue version of the 'Stow'
The Crockett & Jones pic (left to right, back row first): 'Snowdon' veldtschoen boot; 'Arran' boot in rough-out; 'Coniston'; 'Skye' brogue boot; 'Islay' brogue boot
The heavy-duty boot pic (left to right, back row first): 'Selkirk' veldtschoen boot by Alfred Sargent; WW2 Lotus veldtschoen boot originally worn by a Czech officer who fought with the British Empire forces; WW2 Lotus veldtschoen boot originally belonging to a 'T Windows', whoever he might be; CC41-stamped boot made of 'Beva' leather by an unknown maker, dating from 1941-1948
The brogue pic (left to right, back row first): C&J 'Hastings' made for James Purdey; C&J 'Hastings'; Church's 'Grafton'; C&J 'Argyll' made for Hoggs
The Church's pic (left to right): 'Consul', 'Buck', 'Delegate'
The random pic (left to right, back row first): Alfred Sargent brogue for Hope & Glory; Grenson boat shoes; Tricker's suede derby; Alfred Sargent 'Egham' for Shipton & Heneage
The chukka pic (left to right, back row first): Alfred Sargent; Edward Green; Alfred Sargent for Hackett; Tricker's; Loake for Brocklehurst of Bakewell