On licensing, the general principle is that someone acting as a principal on their own contract, and marketing that contract rather than the property, has usually not needed a license. Several states have changed that, and land isn't carved out. South Carolina restricts unlicensed wholesaling where the operator doesn't own the property. Illinois treats a second deal within twelve months without a license as brokerage and a misdemeanor. Nebraska and Kentucky have written public marketing of a contract into their definitions of brokerage. Whether your two parcels put you inside or outside your own state's rule is a question for a real estate attorney licensed there, and it's a cheap conversation compared to the alternative.
Insurance is simpler than you'd expect. You have no title and no insurable interest, so there's no property policy to buy. What operators in this position look at is general liability and errors and omissions coverage, and you should ask carriers directly whether they'll write E and O for an unlicensed wholesaler, because a number won't.
The land-specific trap is access. A rural parcel can be landlocked, or reached only by a prescriptive path across a neighbor's field, or split by an easement nobody recorded properly. Since you never take title, you may not discover any of it until your end buyer's survey comes back and they walk. Order a title search early and ask specifically about legal access and recorded easements. Delinquent taxes are worth pulling too, since the payoff amount comes straight out of whatever spread you thought you had.
