I live on and maintain just under 19 acres here. three are tillable, close to 5 acres are mowed and the rest are wooded. I also own and maintain a 2.5 acre building site about 6 miles away (mostly lawn now). And have a 50+ acre wood lot with lake frontage to maintain that's a two hour drive from the homestead.
All of it's been maintained originally with a 20HP JD 750 and the last few years with the new Kubota B2650. Everyone's situation and uses are different. But in the last 30+ years, I could count on one hand the number of times I wished I had a larger HP tractor. The other 11000+ days have had all the work needed done without troubles and most all of them with a smile on my face!!
Both tractors are ROPS models due to working in the woods and also for keeping the center of gravity lower while mowing ditches. Winters here can be long and sometimes brutally cold. It doesn't take much to fab up a removeable cab complete with heat for those winter snowblowing chores. It's the best of both worlds.
Our two sons have told me that I've replaced them with attachments for the tractor!
I tell them I'd be happy to sell the attachments if they want to move back home and start helping again. No takers yet!!