Well you don't have enough info to say his debt is ridiculous (It is a bad sign that he has helocs on both his residence and the rental) You don't know what income is generated by the rental and we don't know the time horizon or potential on the land purchase. We also don't know what his income is overall. All his interest rates are very low, which is a good sign.
Debt isn't always a terrible thing if the ratio to income is reasonable, the rates are affordable and the goal to making a return is realistic. It's a problem when it's driven up to maintain an unsustainable lifestyle.
Most people would cringe at the idea of borrowing money to buy a stock or an annuity. But they do it every day for real property. Why is one unthinkable and the other OK? Don't both have basic value? Don't both have downside, as well as upside risk?
Many of the posters on this site are of the mindset to be and stay completely debt free. That is a noble goal, but unrealistic for most and can sound judgemental to those desperate folks that are drowning in unmanageable debt.
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