Rick in MS,
I am new to this website (as far as actually posting) but have been around tractors for quite a while (by no means an expert). I base most of my information on the experiences I have had throughout my years of tractor ownership (have made a lot of stupid decisions, but learned from them). I am quite interested in the threads on here about purchasing tractors and most of my posts have been in this forum. I guess the reason is, I never used a tool like this site for buying my tractor (and it is a great tool). I talked mostly with my Dad and some cousins that farm. I drove all over the place and looked at every color tractor out there. I ended up buying a 40 HP tractor for using on 6 acres. Trust me when I tell you a 40 HP tractor is not to big for your land.
The only problem I see you having is justifying the price of a new 40 HP and up tractor. They are EXPENSIVE and you will probably have that payment for somewhere around 4 to 7 years (350 to 550 a month probably). It is a lot to think about and consider. It should be taken seriously and you are doing the homework. A smaller tractor will do the jobs you are talking about. It will just involve a lot more chainsaw work and getting on and off the tractor a whole lot more. I have cleared out a lot of brush like you posted with my tractor. It took a long time and lots of burn piles. I even dug out some big stumps with my loader, just took a long time and lots of back and forth, side to side, and getting on and off the tractor and chopping roots with an axe. Then I had to push and grade all the dirt back over the hole. But again,it can be done and is rewarding once you start seeing the progress. It is a journey and will take many years if not a lifetime to get it the way you want it.
If you do decide to get a smaller tractor do not get a "entry level" one. Buy premium and get the bells and whistles. You will not regret it. You can also add attachments later on as you go along. My neighbor has all kinds of tractors, barns, tools and equipment. I asked him one day how he got all that stuff. He looked me straight in the eye and said "years and years of hard work". I truly hope that you can find what works for you. It can be down right frustrating trying to purchase the "right" tractor. I will tell you this, if i could afford it I would get a bigger tractor and a backhoe, but I don't regret for one minute buying the tractor I have now. If I could afford a bigger tractor I would still keep the one I have now. It has been a great tool for my property and has never let me down. I wish you all the best in your decision on buying a tractor.
By the way: Former Seabee here. Gulfport MS. Hoo RAHH!!!