I applaud your want to be independent and respect your dad. I had a similar situation many years ago. Fast forward to the present, my Dad is thrilled to see us doing our hay deal. I'm a firm believer in using what belongs to you and if it breaks, no who struck john afterwards.
With a full time job, even a 5 acre field, rejuvenating it, acquiring and refurbing old equipment can occupy all of you're spare time.
I recommend hay. Reason it - you can walk away from it. Live stock requires attention, grass needs mowed and baled. You can sell you're hay and recover you're investment.
When we started, the idea was, fix up some junk equipment, expose my boys to haying, let them turn a wrench. But as we continue to wade into it, we see potential income for college expenses. Once my kids are on their own, my intent two fold - one slowly upgrade equipment so we are not wrenching on it all the time and building an equipment/shed foundation should my family want to continue after I take up a rocking chair - such that they don't have to spend a dime on a piece of equipment. I'm also excited about haying and all aspects of it to give me something to do when I retire - much better IMHO than planting myself in front of a TV.
Said all that to say this:
Find you a few acres. Get a tractor or two and equipment. Make it a hobby and family ordeal. Some of the best quantity/quality time we've had last couple of years has been haying. Keep an eye out for excellence in your hay (if you go that route) so you can get top dollar. Start small and grow as you choose. Most of all, have fun!
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Today's Featured Article - Restoration Story: Fordson Major - by Anthony West. George bought his Fordson Major from a an implement sale about 18 years ago for £200.00 (UK). There is no known history regarding its origins or what service it had done, but the following work was undertaken alone to bring it up to show standard. From the engine number, it was found that this Major was produced late 1946. It was almost complete but had various parts that would definitely need replacing.
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