I will admit to not having read the whole thread, but my answer is "no".
(1) The price you're paying for what you're getting drops disproportionately as you move above the size that many "new to tractors" folks think is "too big". If you don't have to trailer it (for a landscaping side-hustle or something), or if you aren't having to deal with very limited space to store it, bigger is better.
(2) More weight and power does more work, and it is safer too. Small loaders tip over easier, small tractors roll over easier when mowing slopes, invariably using too small of a tool tempts people to attempt things they shouldn't.
<snip>
This.
I read all 8 pages of posts and disagree with so much of the advice given.
For your situation I'd find a 100 HP or so Kubota 4x4 with loader. Always buy 4x4. Cab is great. Buddy seat is a good safety option. Get implements sized to that tractor.
I did nearly what you are proposing. Got the 95 acres (25 is field the rest timber), bought big machinery as it was a 200 mile commute for me and I only had a day or so a week to get anything done.
Started with a used 33 HP Kubota with a loader. Bought brush hog and tiller. Kubota is so worn out now that I need to cut off the ball swivel ends of the lift arms and weld new ones on just from mowing. That tractor was way too small.
My dad was right, the larger the machine, the safer they are and easier to operate. I started running a Case 450 dozer by myself at 11 years old, my dad just showed me how to operate it, left me with lunch and water on my 11th birthday and said, "you'll remember this". Later I graduated to a D7 dozer and was amazed how much work I could get done and how much safer it was.
I had an 80 HP David Brown my dad gave me before he died. Was a great tractor but nothing compared to the 110 HP Deere I just bought. It gets used more than anything else here. 100 HP is not too big at all.
My garden is 1 acre and I till it with a 150 HP John Deere and a 22' heavy disk. Doesn't take long.
For field work I just bought a 235 HP Steiger articulating 4x4. Overkill for 25 acres but my 150 HP Deere just wouldn't pull the plow and ripper through the heavier ground. The Steiger gets right to it.
My wife and guests like the 150HP Deere 4630 as it rides smooth, easy to operate, has a nice cab, working AC and a radio. I have no trouble getting someone to put in 3 hours do disk the field. I won't let any of them use the little tractors, too easy for them to get hurt on them.
Pretty much every working farm has children riding in the tractor cab with the parents all the time. Those farmers are raising adults, not children. Those "kids" can safely operate those machines from a very early age, mature early and learn responsibility. Just the other day I met a parade of 4 new John Deere combines coming down the road with a matching set of dark haired teen and preteen girls driving them down the county road. Those girls were operating half million dollar machines and paying very close attention to the work at hand. Wait until you are comfortable with the tractor then let the kids learn to work with you.
I mentioned a 100 HP Kubota above, John Deere is also great but I do like the interchangeability of the skid steer attachments for the front loader. My 110 HP Deere doesn't have that.
I'd avoid any other brands. I've owned, operated and repaired almost every brand and parts availabilty and dealer support is best with Orange or Green.
Finally, plan on getting a backhoe or excavator. I've got a Caterpillar 416D backhoe. It's tough and gets worked like a rented mule around here. Remember, a Loader is not a Digger. Farm tractor loaders are great for moving and spreading loose material but you can break a farm tractor in half trying to dig with it. An excavator in conjunction with a 100 HP tractor loader would work great.
Our Deere dealer has a great financing program for both new and used tractors. My Deere 6115 is a 2013 model, open station and no DEF. Wish it had a cab and a buddy seat.
My current tractor lineup is
33 HP Kubota, worn out
80 HP David Brown, tired
110 HP John Deere
150 HP John Deere
235 HP Steiger
8000 lb Pettibone telehandler
Caterpillar 416D backhoe
I'd like to add a 50 HP utility tractor at some point but what I have is getting the job done