I've been planning on going with nearly new gear for that reason. Pay now, or pay later. Newer gear has more creature comforts.
Max distance to drag wood is 1/4 mile.
"Nearly new" gear is fine but it's still prone to break downs. It's not "if" it's "when". Even nearly new machinery still requires maintenance. And ask yourself why that "nearly new" machine is for sale in the first place. If it's a repo or leaser you can count on it having been run hard and neglected.
The people here have given you a good idea of what to watch for and they made good points. You very obviously know very little about what you're doing. You have a vision of what you want for a result and that's good but without some skills and some basic practical knowledge you're going to wind up spending more money than you'd planned. A lot more.
A couple of other things to consider...and these come from personal experience. Can you do your own wrenching? Do your own oil changes and filters? Can you make up your own hydraulic hoses? Will you have the start-up cash flow to keep a supply of spares on hand? Do you have fuel storage and will it be delivered or will you have to travel for it? In logging it's not maintenance that costs, it's the downtime that kills you. If you have to run to town for a filter or a hose or fuel you can kiss the profit for that day, and maybe the couple of days, goodbye.
You talked about creature comforts and needing an AC cab. That's fine but fancies don't make you any money. Are you prepared to log, and log
hard, all day and then work on your machinery at night? Are you willing to log all day, work all night, grab an hours sleep in the pickup and then log the next day again? There are times when that's necessary. On a hobby-logging set up like yours I doubt if you'll have the extra cash to pay a field mechanic.
Just by a rough count you've been given the combined experience of over 200 years in the woods by the people who have answered your posts...in this thread and the others you've started. You need to listen. You need to listen soon, too.. You need to realize that just because you want to do something a certain way, or with a certain kind of equipment, bearing in mind your total lack of experience, you'd be well advised to take advantage of the help that's offered. Don't ask for our opinion on something you know nothing about and then argue with us. That's rude and insulting. It only underscores your lack of experience and makes us reluctant to even bother with you.
There's good help and advice here, free for the taking. Or, just stumble blindly on. Your choice entirely.