We have a farm that is held by an LLC. We intentionally wanted to make it hard to sell shares. We did not want a situation where one of the owners would get upset or in a financial bind or something and sell shares to the highest bidder who may have a very different hunting ethic than the rest of us have. So, what did we include in our LLC agreement? The first right of refusal. We also have a minimum shares threshold for owners to have access to the land for hunting and other recreation. This means an owner trying to sell must get a legally binding offer good for a specified time period. The other owners then have an opportunity to declare if and how many of the shares they will buy at the offer price. So, the outside buyer may or may not get enough shares to have access to the farm (other than financial). So, the outside buyer takes a risk when he makes an offer. This devalues the shares to a random outside buyer. This protects the interests of the remaining owners.
This seems at first like a real handicap but it isn't. It forces a selling owner to take into consideration the other owners before selling. He simply needs to find a buyer with a hunting philosophy aligned with the other owners, and socialize him with the other owners. Once they get to know and trust him, they have confidence his philosophy is similar to their own and the perspective buys has confidence they won't leave him hanging with too few shares to be able to use the land.
There are situations where right of first refusal can be a good tool, but think about it from a buyer's perspective. Why would I as a buyer do all the research and make a top offer for a property when I know, someone else can come in an offer the same price as me and get the property. There would need to be some real incentive to buy the place. If I have several candidates, knowing there is a first right of refusal on this property would be a negative.
So, if I'm the seller, why would I want to do anything that could dissuade a potential buyer from making me his best offer? The only reason I can think of is because I'm making money doing it. So, it depends on how much you want the land. I'm sure if you offered him enough cash for the right of first refusal, he would probably sell it to you.
Personally, I'm with many other posters. If he has already sold land to you and you both are happy with the transaction, simply let him know you are interested and ask him to let you make a offer before he sells it to someone else. That is probably your best bet.
Thanks,
jack