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Scenario $2$: Questionable Conservation Easement & Charitable Intent

Taxpayer owns a plot of land with questionable ecological value. Original basis: $$200,000.$

Donates a conservation easement, drastically restricting development.

Aggressive appraisal values the easement at $$1\mathrm{.}5$ million, resulting in a huge potential charitable deduction.

Taxpayer has a $$50,000$ NOL carryforward from a previous year.

Other income:

Wages: $$300,000$

Qualified Dividends: $$15,000$

Itemized Deductions: $$45,000($excluding the potential easement donation$)$

Allowable deduction for self$-$employment tax: None

Questions:

Discuss the red flags that make this highly scrutinizable by the IRS.

If the deduction is partially allowed, how would the NOL carryforward interact with the income limitations for charitable deductions?

If the deduction is disallowed, what are the potential penalties the taxpayer might face?