There is a heavy, barred door in a sub-basement that leads to the dungeon and a watch is always posted to prevent incursion from the depths. It appears to be a series of ancient crypts but some investigation reveals a more extensive structure beyond, both worked stone and caves. CJ knows the dungeon is larger than the crypts but is unaware of its size and depth.
CJ allows adventurers access to the tomb in exchange for a share of the treasure. He requires an up-front payment before entering because money. And then another payment on exiting because more money. He may allow entrance without the fee on a case by case basis. But this is dangerous because he is much less willing to let freeloaders exit without due compensation. Parties that return several times with good hauls might be exempted from the entrance fee. CJ is willing to forego that pittance for his share on the back end and the good PR. Somewhat like businesses give free stuff to celebrities to drive a greater increase in business.
There is a slot in the door to pass a bag of coins or other payment. Can't pay? The door stays shut. Are you being chased by monsters and think you can find safety through the door? Door stays shut. CJ is not motivated to needlessly endanger his guards to fight your battles. Trick the guard into opening the door and monsters attack? You are executed (or banned at best).
CJ is motivated to provide numerous services in exchange for a cut. Infirmary with healer. Armorer and weaponsmith. Adventuring supplies. Cosmopolitan town filled with fodder ... er, riff-raff hirelings. Anything beyond the keep's ability to provide can be obtained with enough time and money via the trade city to the south. Goods can come with the normal provision deliveries or be expedited for a fee.
In addition to the tomb, to which he controls sole access, there are several other sites of adventuring interest surrounding the keep. These are more dangerous to reach (they are not inside a fortified, garrisoned keep) but may offer greater rewards and an escape from taxes. Maybe an escape from taxes. Once he finds out his delvers are plundering outside dungeons, he will explain the need to continue contributing to the upkeep of the castle and the garrison that serves as their home base and protects the community. And he is right.
CJ wants to build the keep into a village into a city into a kingdom. He knows that successful delvers will bring his dungeon, and thus his keep, fame and notoriety. He also knows he needs lots of money to build/repair the keep, pay the garrison, and eventually expand.
Why does CJ not delve? He has better things to do. Building the keep is a full-time job and endangering his life in an old crypt is very poor ROI for him. However, unknown to most, CJ does patrol around the keep eliminating threats that would outclass his garrison.
Several denizens of the Keep believe those who enter the tombs are cursed. No specific reason, just seems like the kind of thing that should happen when you defile a tomb. They likely will not remain in town for too long (or will seek to murder the party to end the curse).
One hopes the players will try to improve the well to facilitate entering and exiting the dungeon. Something simple like an iron ladder would be easier than climbing a rope. What if they find treasure that is more than 4 feet wide? CJ will need funds to make improvements.
He will insist on security, though; a retractable terminus to keep dungeon things in the dungeon. Maybe build a fortified entrance at the bottom so delvers are not exposed while trying to haul up bulky treasure.
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