I have less tractor than You and still get the job done easily. I run a vintage NH 479 mower ($2,000), a really vintage JD 14T baler ($500) a NH 55 rake ($600) and a NH 1012 stackwagon ($2300). Wear and tear parts come from Rural King or TSC or the JD dealer or ebay.
Lot more fun if you have help from customers, neighbors, or teenagers. I get $3 - $4 per bale depending on delivery or help. Put up 600 - 700 bales per year. do the math.. Run it as a 'business' for tax reasons. I sell out every year. Most customers have been with me for 20 years or more. Buy tools, welder(s), air compressors, you name it, to support the farm. The only skill you need is to read the weather. Just about all weather forecasts are entertainment value, not hay production value.
Best approach would be to tag along with a small, local hay producer to see what is involved. High value if you have animals of your own to feed.