Men, and some women, love these activities. I do not mean lawn-mowing, I mean meadow maintenance without grazing animals on the land. Yeah, ideally you want cattle. Have you even found a pile of snake eggs beneath a cow pie? I did, once.
In New England, we have become so accustomed to the pastoral sight of meadows and fields that we forget that they are not natural. These were created out of the wilderness with tremendous effort for grazing and farming. Neglect them for 5 years, and they will be beyond repair because nature wants them to become woodland again.
At the farm, we have had meadows suitable for haying or grazing, areas that require annual brushwacking (because more brush than grasses in those areas), and steeps that need scything or something similar.
These sorts of land maintenance are deeply satisfying and, with machines, deeply relaxing with a cold beer or three. No lifting, work gets done. Somebody observed that open field maintenance is like running one's hand over the curves of one's beloved.
Haying for real hay is tricky. Timing is everything. Around here, July for commercial haying. You need the hay to go to seed, and then you need to let it dry after cut before the baler. No rain. Stored wet hay can spontaneously combust in storage, or, at least, turn moldy. You know that already.
With the dairy business moving out of New England, and horses fewer and fewer, we had no market for hay. We switched to conservation mode which is a non-economic mode.
The non-economic conservation mode for open-space maintenance is based on the idea that meadow critters (meadow-nesting birds, rodents, snakes, etc) are pretty much done by late July. However, many wildflowers are at their best in July and August and the bugs and butterflies rely on them.
We recommend mowing/brushwacking non-commercial, ungrazed meadows once per year in early September or late August. Let the mowings lie. They will mostly disintegrate by April.
If you like walking paths, keep them mowed like lawns, about 8' wide paths so you can stroll around your grounds with a coffee or whisky and ceegar without getting soaked with dew or infested with ticks while bird-watching.
We had a wet meadow in a flood plain along our trout stream (with trout pool for swimming) where the grasses and sedges grew so thick that once/year was not manageable. We had to brushwack that 5 acres patch twice/year or the machine could not handle the density of the lush growth. I was sadly aware, though, that the wetland meadow critters (Wood Turtles, Leopard Frogs, snakes, toads, etc) did not appreciate that at all and I felt bad about damaging that habitat and sometimes killing them. I wonder if it might have been left well-enough alone, but it's just what we always did.