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Certainly not an air problem. Top off master cylinder, bleed and you might just get lucky. Do yourself and your brother a huge favor. Build or have him build a power bleeder. Huge help. Since you have time, I'd order up a gallon or 3 of surplus silicone brake fluid (BFS).
First thing you need to do, besides brakes, is get rid of those funky tires and put some NDTs on it. I'll speed right over with my air jack and big impact and give you the tires right off my truck. I'll even haul off those tires you have there. LOL. Seriously, looks good. Was it a GL...