Racing sounds a lot like farming. :)
Up here in Minnesota we have very different conditions, too much water 8 out of 10 years, heavy clay soil. So I'm probably not going to help much with the equipment you need.
But we do full tillage up here as well.
I have hopes strip till will come around some day, but - still doesn't work well with our soft wet cold clay. We need to beat the ground into submission to get it to dry out & warm up.
I would guess in 3-4 years you could sell that stuff for about what you paid for it, and move to something different if you wanted to, so you wouldn't be out a whole lot along the way?
I've just spent about $25,000 a year for the last 4 years on tiling my small farm, for the very same reasons you state with the irrigation: There is a lot of regulation on such things, and it only gets worse. I've seen that in just the past 5 years, more hoops to jump through, more officies to visit. Like you say, it will be stopped some day, and that is that. It happened before - in the mid 1980's they stopped anyone from draining a wetland any more. If you got it done by then, you're good, keep tiling, keep farming, but now - it's just wasteland.
So, if you will have that 60 acres in ag production for the next 20 years, and you have the means to put in a well and a pivot, it would seem to be a good investment now. Whether you farm it or you rent it out, you should be able to recover the costs over the next 2 decades, and improve your bottom line.
But I don't know anything about irrigating, we do the opposite here, tile to get rid of the dang water. 'Here' tile is a great investment. I assume 'there' irrigation is a good investment.