Welcome to TBN... we were all rookies once!
Prior responses are dead on... I can add a few ideas:
1) Go to dealers and drive different tractors.
2) If you have a buddy with a tractor, maybe he will let you drive his and use his equipment to get a feel for how it all works together.
3) A tractor is just an engine... it is the attachments that personalize it and let you do what you need done. Be sure and include all the implements you need at your initial purchase so you can begin benefitting from your purchase immediately.
4) read, read, read, what has been said before here at TBN... it is a treasure trove of experience, comments and opinions.
5) Don't rush... you will live with what you get for a long time...
Now, for my opinions. Bigger is better. More horsepower is better. Go for what you really need, and more... you will discover that you truly needed it in the first place.
Myself, I had never had a FEL, HST or cab and considered them a little much, but got them because it was a package deal. I couldn't be happier.
I can highly recommend a Grand L 5030 HST with cab, FEL, rear lights, 4WD, at least one rear remote (more is better). I've been able to outfit mine to do all I need done on 200+ acres