Proper leather shoes

I'm struggling to choose between a pair of boots and thought that lfgss might be able to help me overthink it.

My feet are like little spades (gardening not playing cards). Very wide. All my shoes start tight and end up spilling out at the side. But now I have self-respect and I want a well-fitting pair of boots that will last 10+ years.

It wasn't easy finding wide boots. I got these both on sale for the same price - Tricker's Grassmere in tan and Cheaney Pennine II R in "burgundy". They're both G fitting, or as tricker's likes to call it, 6.

Despite being 1/2 size smaller, the tricker's are bigger than the cheaney, on the outside at least. The sole is 7mm longer & 3mm wider (both are commando). The tricker's feel higher quality overall - the leather is thicker, the top of the tongue is lined. But surprisingly the cheaney are more immediately comfortable with less pressure at the widest point of my foot. What's going on there? Some theories:

1. The cheaney are "veldtschoen" with the upper leather bending outwards. The tricker's are storm welt with the upper leather bending inwards + a layer of welt on the outside. Do these methods make the insides of the shoe wider/narrower respectively?
   
2. The cheaney leather is more forgiving, allowing my foot to overspill without feeling it as much. Does this mean they won't last as long?
   
3. The cheaney last shape fits my foot better. It's boxier, so maybe more height near the toes. But tricker's last looks wider all round.
   
   

Basically I'm leaning towards the cheaney because they feel wider, but is it an illusion? I'm sure I could break in the tricker's. Is the thicker leather worth it in the long run?

Other questions:

The tricker's heel is much wider and has a thick layer of leather in it, the cheaney is all rubber. Is that just aesthetic?

How easy/cheap is it to find a cobbler to resole veldtschoen vs storm welt?