I don't see where you stated the price you have to pay to keep it in the family, or did I miss that?
If you treasure the memories of your Grandfather and the tractor, and you can keep it for a price that's at all reasonable, BY ALL MEANS DO IT! You can sort through the issues one at a time, as time and $$$ permit.
Most of the issues you mentioned are cosmetic and/or can by dealt with reasonably with used parts or aftermarket parts.
The brake issue may be a bit more serious.
A "brake problem" could be as simple as the brake valve needing an overhaul, or as serious as the brake pads have lost their linings and the brakes have gone "metal-to-metal", which would leave the entire transmission, final drives, and the hydraulic system full of brake debris and metal filings.
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