New regions.json key: entrance_rules. Allows you to make entering a region cost different things based on where you're coming from.

schemas/Manual.regions.schema.json

@@ -39,6 +39,32 @@
                             "type":"boolean",
                             "default": false
                         },
+                        "exit_requires": {
+                            "description": "(Optional) Additional requirements to use a specific connection out of this region.",
+                            "type": "object",
+                            "patternProperties": {
+                                "^[^$].*$": {
+                                    "type": ["string", "array"],
+                                    "items": {
+                                        "$ref": "#/definitions/Require"
+                                    }
+                                }
+                            },
+                            "uniqueItems": true
+                        },
+                        "entrance_requires": {
+                            "description": "(Optional) Additional requirements to use a specific connection into this region.  This is the same as exit_requires, but from the other side.",
+                            "type": "object",
+                            "patternProperties": {
+                                "^[^$].*$": {
+                                    "type": ["string", "array"],
+                                    "items": {
+                                        "$ref": "#/definitions/Require"
+                                    }
+                                }
+                            },
+                            "uniqueItems": true
+                        },
                         "_comment": {"$ref": "#/definitions/comment"}
                     }
                 }
@@ -69,4 +95,4 @@
             }
         }
     }
-}
+}

src/Rules.py

@@ -1,5 +1,5 @@
 from typing import TYPE_CHECKING, Optional
-from worlds.generic.Rules import set_rule
+from worlds.generic.Rules import set_rule, add_rule
 from .Regions import regionMap
 from .hooks import Rules
 from BaseClasses import MultiWorld, CollectionState
@@ -234,7 +234,15 @@ def fullLocationOrRegionCheck(state: CollectionState, area: dict):
                 def fullRegionCheck(state: CollectionState, region=regionMap[region]):
                     return fullLocationOrRegionCheck(state, region)
 
-                set_rule(multiworld.get_entrance(exitRegion.name, player), fullRegionCheck)
+                add_rule(world.get_entrance(exitRegion.name), fullRegionCheck)
+            entrance_rules = regionMap[region].get("entrance_requires", {})
+            for e in entrance_rules:
+                entrance = world.get_entrance(f'{e}To{region}')
+                add_rule(entrance, lambda state, rule={"requires": entrance_rules[e]}: fullLocationOrRegionCheck(state, rule))
+            exit_rules = regionMap[region].get("exit_requires", {})
+            for e in exit_rules:
+                exit = world.get_entrance(f'{region}To{e}')
+                add_rule(exit, lambda state, rule={"requires": exit_rules[e]}: fullLocationOrRegionCheck(state, rule))
 
     # Location access rules
     for location in world.location_table:

src/data/regions.json

@@ -6,6 +6,12 @@
     },
     "Second Region": {
         "requires": "|@Characters:1|",
+        "connects_to": ["Third Region"],
+        "exit_requires": {
+            "Third Region": "|@Characters:5|"
+        }
+    },
+    "Third Region": {
         "connects_to": []
     }
-}
+}