Maps aren't working so I'll just try to be as descriptive as possible.
About half of a days travel to the south-east is a small apple farm run by Thealdan. You doubt there would be much in the way of equipment or money there, but that also means little to no guards. Hell you might even just want to send the diplomat and swordsman there and extort them for weekly payments, of course you could just burn down the entire farm and loot the food, but that's a little less suttle.
About two days to the north is Wyvernville. Named for the wyvern who killed goblins seiging it. It has around 300 citizens. There is a small amount of guards posted in the mayors manor and the markets. Since your still legal you can visit this town all you want. You know you'd need at least 30 skilled men to siege, capture or loot this town.
About 2 hours to the west is Glasswater Forrest. Named after the elven mage that lived in the lake. You could hunt and forage around here without to much danger apart from the occasional bear.
About 4 hours to the east is Greyhall Mine. It is probably only slightly guarded and has only the money required to pay the running costs on location. The 'workers' are actually enslaved dwarfes who didn't have enough money to pay their debts. They may have smelters in the mine. If you take this you would have a huge increase in ore and bars of metal.