Pay up for a parcel with a lease that carries the taxes, or buy bare and eat the hold?

The wooded one is where the scope creep lives. Nothing cleared means no one has walked the drainage, and you don't know where the wet spot is until a surveyor's boots are in it. On the reno side I've learned to pay for the parcel someone has already been maintaining for thirty years, because maintenance is documentation. A row crop tenant has told you the field drains, drives and doesn't flood, every year, for free.

Income during a hold is worth more than the arithmetic says. I've held land through two stretches where I would have taken a bad price if the tax bill had been the only thing arriving in the mail, and the lease is what let me say no. That's the whole strategy on my end, patience you can afford.

But $152k of basis is not a rounding error on a three lot split. Four lots on the cheap parcel at $95k each is $380k against $213k. The same four on the leased parcel is $380k against $365k, and you have not been paid for eighteen months of work. Unless the leased parcel's lots are worth materially more, the $7,400 a year is buying you a much worse deal.

Orchard's math is the whole thread and it says the lease is nearly irrelevant. Eighteen months of $7,400 is $11,100. The basis gap is $152k. You'd need fourteen years of hay money to close it.

The only way the leased parcel wins is if its lots retail higher, and you've given a reason to think they might: paved frontage on cleared open ground versus a 40 foot access strip into woods. Cleared level lots on a paved road usually price above wooded interior lots off a strip, sometimes by a lot. Price both sets of lots properly before you compare basis, because that's the input carrying the decision, and the $185 an acre cash rent is close to noise.

Question before either. What does the lease say about termination on sale, and what notice does the tenant get? In some states a crop tenant has statutory notice rights that run to a specific date, and if you close in the wrong month you may owe the tenant a full season before you can disturb the ground for survey or road work. That's a schedule risk on the very parcel you're buying because it looks patient, so have a local attorney read the lease before you rely on the income or the timing.

Also ask what happens to the agricultural classification when you plat. In my county the rollback tax on losing that classification came back three years deep, and it took two years of lease income with it. Nobody mentioned it until the assessor's letter arrived, and the rules on rollback periods vary by state so check yours specifically. Not fatal, but the leased parcel's income is smaller than it looks once you net that out.

Cheap and wooded is most of what I look at, and the 40 foot strip is the part I'd spend the week on. Confirm it's fee simple and wide enough for whatever road standard your split triggers, because a 40 foot strip that has to carry a public road standard is a dead deal at closing. If it works, that parcel is the better buy and it isn't close.

The framing I'd push back on is treating income as protection. It only protects you if the money is actually there when you need it, and a cash lease pays once a year on the tenant's schedule. If your bad month is March, $7,400 arriving in December doesn't help. A cash reserve you set aside at closing does the same job and costs you nothing in basis. What the lease genuinely gives you is a better looking file if you're borrowing, which arbor already said, and that might matter more than the cash does.