So John is probably “worth” over 100M but he is also cash poor. The same financial situation was shown on Downton Abbey. The English Lord has a Yellow Stone Dutton Ranch shirt but that doesn’t mean it’s profitable. Mark Zuckerberg is “worth” billions in Facebook stock but that doesn’t mean he has that much cash to spend.
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There is a big difference between being “worth $X,000,000” and Yellow Stone Dutton Ranch shirt. The ranch is worth over 100M but the cash flow from selling cows could be barely able to make weekly payroll. In season 2 Jenkins ask John to buy him out but John says “I’m not a rich man despite what people think.” John couldn’t buy that much land without borrowing against the ranch itself.