... My ideas of what I want were more refined today. ...
So glad to know that you are careful to consider some really good advice here. I have some notes to add. I've had my ranch for 24 years and have owned 7 tractors of varying sizes - 25 to 130 hp. Have plenty of woods.
A cab to deal with summer heat (where I am) or cold of winter makes a lot of sense if that is when you will be using your tractor. If you intend to do snow handling with a pickup, then maybe you won't have as much cold weather use. Or is that just short term?
You mention a lot of wants for tractor tasks. You don't need all of the attachments now, but you don't want to change tractors in the future to add something you think you need, so make sure your tractor 'can do it'. Assuming you want to use a snowplow/blower, normally with HP comes weight, which snow conditions need, so I would shy away from a tractor that is less than 3,000 lbs, and ensure it comes with a mid-PTO. Weight and size is also good for handling trees and tree parts. Also, for snow, watch the tires. R1 is much better than R4 or even R14, for snow or dirt or especially mud. You are not running up and down hard roads or doing a lot of loader work on concrete, so wear is a non-issue that may make some question R1.
Get the tractor with an OEM loader. Indispensable.
I bought a used a 25hp tractor with box blade (BB). Only used the BB 2-3 times because I found it not useful. It only pulls perpendicular because it cannot angle, and without adding hydraulics or manually cranking a 3 point arm, even tipping to drop the left or right edge is not going to happen. BB is not recommended unless you have an unspoken need. It will not help you with your road.
If you need help with holes for plants/trees, consider a post hole digger. It is essential if doing real post holes and can be used to dig a shallow hole for plants, then you can manually trim the edges away with a shovel until you get the diameter you want. If this is a common activity then do consider a front loader spade as you have mentioned.
A backhoe will be of limited use because if you intend to use the 3 point arms on the tractor, you must change everything out (most models). That is very time consuming and a PITA.
I bought my last 6 tractors as used on Tractorhouse.com. Tractors are not like cars - they are built to endure decades of use and do not become obsolete. If you target a low usage tractor, say 1000 hrs or less, you can get a lot of tractor for each dollar with low wear and high reliability. There are even dealers that can finance a used model. As for brands, some people say JD and Kubota are high dollar, but I say that through experience, customers have found out what will last, has reliability, unlikely to break or fail, has parts and service, and what has better resale value. They are willing to pay for those benefits.