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I'm in Kentucky...similar weather to you. I use a Reese drum mower..6 ft cut. It takes a lot of horsepower in heavy grass.
If you don't have a tedder you will lose hay quality and get some wet when an extra day of drying time is needed. You can buy a decent 2 basket tedder for under $1000. He is 14..he has time...he is not a BTO yet! A few extra hours in a tractor seat won't hurt him and with smaller and older equipment he will learn the business and not spend all his earnings on equipment payments. Sadly, a sickle mower will just be a huge frustration. Lots of the guys on this forum started with a small tractor, old haybine, cheap rake and old old baler. It is a little slow, but cheap. Be on the lookout for a few wagons to put the hay on. Hopefully he can sell it out of the field to people that load it themselves to save money.

Have fun! I started making hay at his age, and still do it because it is very gratifying to see a barn full of beautiful homegrown hay.
 
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