Haha love that one. I did go over the 150 rule for a tractor but I had a specific use case for it and it works well. Love the Mad Max tractory ^^
I've lurked here a lot but never posted before, but this one seemed to need another perspective. Most of the posters did not read or pay attention the OPs points.
1. He has very little time. Get a big tractor, get the work done faster. I've dinked around plenty on little tractors, they beat you up on rough ground and take way longer to get the job done. Just try spreading rock or leveling something with a small tractor vs a big one. Huge difference.
2. Child riding on the tractor. Lots of dire warnings. OP is former service and an ER nurse and seems pretty capable of assessing and mitigating the risks.
3. Learning curve. I can say for a fact having run a lot of big and little equipment that if you have depth perception a big tractor is easier and safer to run.
4. Cabs. OP wants a cab for comfort and safety. Get a Stihl pole saw and have your wife drive you around in the back of the pickup and take down any branches that will hit the cab. First thing I did and I repeat the edges of my field and roads every second or third year. It's maintenance.
5. Leasing out the ground. OP stated that he didn't want someone farming the ground around his house which is half of it and is very understandable. Those telling him to rent it out didn't read his posts.
6. Road building. If OP can stabilize a gun shot wound which he probably has plenty of experience with, he can learn how to properly grade a road so it will drain. Pro tip: Always put down geotech fabric under your rock. Depending on your base soil you can use half the rock and it will last much longer. Watch youtubes, maybe hire some of it done so you can watch. People have been building good roads since at least Roman times. Not hard.
I know well how the crowd here leans towards little tractors, that's what this forum is about, but the OP was asking about bigger tractors. I didn't figure I'd earn a lot of love over my perspective, but it's a different one and perhaps useful to the OP.
OP, suggest posting your question in the Machinery forum at New Ag Talk and see what kind of answers you get. When I posted there about the 225 HP Steiger tractor I was considering buying, one poster suggested I get a rototiller for it and till the garden reaally fast.