I think the million dollar question is - are you mechanically inclined (or willing to learn) and are you the type of person who enjoys doing their own work?
If you are comfortable working on it in your spare time a bit, an old tractor is a great way to go, just do your research and make sure you get a model with decent parts availability. For the most part, they are simple to work on, just require a decent set of tools and time with grease on your hands.
If you would be trailering it into the dealership for any work done, get a new or newer tractor.
A .5 acre lawn is not much, so I would just find a 'normal' riding mower for it - if you don't have turf tires on a 'real' tractor, it can lead to excess soil compaction which isn't great for your lawn, plus mowing with Ag tires when the ground is wet makes a mess.
Past that, you could get by with anything from a small 30hp Massey 35 up to a 60hp tractor for most of the work you've listed out. A larger tractor with a larger brush mower will cut that 22 acres of 'not pasture' much quicker, but a smaller tractor is more manoeuvrable.
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Today's Featured Article - Tractor Profile: Silver King - by Staff. Silver King tractors were produced by the Fate-Root-Heath Company of Plymouth, Ohio. The company was founded by John Fate in 1884 and was originally called the "J.D. Fate Company". After several mergers over the years, the final company name of Fate-Root-Heath came about in 1919. The first tractor produced was actually called the "Plymouth" tractor and was powered by a 20 HP 4-cylinder engine with a 3x4" bore and stroke. The four speed transmission had a top speed of 25 mph! After more t
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