embuggerance - I love it!
I don't see going further on the front end than the forks and the bucket. I've spend 16 yrs with an 8n and no FEL at all. I think I'm good with the fork and bucket arrangement. I'm going to gamble on it anyway.
Thanks.
Now to resolve loaded tires or chains, and the tire position questions. With those, I should have it all figured - I think.
Well the QA question has been asked and answered (several times) - Get which ever suits you best but definitely get a QA of some sort.
Now - to address the rest of your questions / comments. Our first tractor was also an 8N - still got it (just finished the hydraulic rebuild last Sat - fun stuff). My father bought it when I was in my Preteen years. I'll be 45 this year, so to say I have grown up on it would be fair.
We just upgraded to the Kioti in Late fall '15 and I can promise you, no matter how well you got by with the 8N, you'll marvel at all the "stuff" you can do now that you couldn't before. So don't discount those with the "plan ahead" advice. My father fell into that trap and will today admit (albeit very grudgingly) that we should have gone one step larger. That being said I still love the CK and it will do what ever I need, sometimes I just have to make more trips
Loaded tires vs Chains - Load the tires. You'll need counterweight for the FEL anyway, it's a relatively small cost in the big scheme (most dealers will include it in the price), and you can always add chains later if need be.
Tire position (I'm assuming you mean width) I have been to IA a few times and I know you're a teenie bit flatter than us hillbillys in SW VA, but unless you have some other reason / restriction for keeping them narrow, the extra bit of stability the wider stance gives you is worth it.
And lastly - let me second (third, fifth, whatever) the advice on a grapple. I wanted one before we ever started tractor shopping. It took me a year of having the Kioti before I could convince Dad it would be a good thing. Again today he admits I am right (very slowly and after much prodding). And as someone who also has pallet forks - unless you have a specific use that only forks will do (for us it's moving hay bales) then skip the forks and get the grapple.
Dad thought we could get by moving brush, downed trees/logs, etc. with just the forks (so we bought them first) and you can if you work at it but the grapple makes it so much easier.
I will add that putting a thumb on your bucket, forks, or having it movable between both is also a viable option that others here have done. I simply had a need for the root / rock gathering abilities of the grapple also.
Well - these are my thoughts and opinions - worth exactly what you paid to get them and double your money back if not satisfied.
Whatever you choose to do I know you're going to be thrilled with the upgrade and I wish you many happy years tractoring with it.