Addendum:
As hinted at by my last question, I would take a very different approach to the Merchant Empire. You know who makes the real money? Bankers. My ME plan would go something like this:
1. Get a lot of money for starting captial, either by intensive chakra beast hunting, a one time robbery, or some other means.
Gathering initial supplies seems essentially the same as what I had in mind, but being a banker requires a decent reputation. If we just try to lend people money and accept us to pay us back, we are asking for trouble if they want to screw us. By gathering materials for merchants to sell from the environment initially, we don't have to worry about the merchants abusing our starting investment too much; we can always gather more stuff. We cannot, however, gain an appreciable sum of money at the same amount of risk.
2. Find a promising merchant with a good business plan but who lacks local connections.
By "promising" do you mean full of personal potential? Otherwise, how could such a promising merchant not have contacts in his home village?
I'd like a bit more elaboration on this section, if you don't mind.
3. Loan the merchant the money he needs and also ninja services to help get his business a small advantage. Also offer some mild sabotage of his competition (ruining their goods... no murder or anything) or spying for him to get him information that gives him a leg up. Use all the precautions Dictator4Hire outlines in interacting with the merchant.
How do we know how much money he needs? How do we know that he isn't cheating us by asking for more money than he really needs, and pocketing the rest? With material goods, we can identify the average price a normal merchant sells his wares at and his profit margins with a bit of mercantile espionage or having Keiko run enough numbers.
4. Collect repayment of the debt at a high, but not unreasonably high, rate of interest.
How often would we collect from any such debt? If we do it too often, we won't be making enough money to be worth our time, but if we wait too long the person whom we loaned money to might just try to leave and escape his debt to us. With material goods that he cannot transport himself, a merchant would be forced to work with us if he ever wants to relocate his enterprise or suffer huge losses to do so, which, if he is greedy, he won't do, which is exactly what I want from him.
5. Repeat process with other merchants until we have a whole network of merchants who owe us money and the success of their business due to ninja aid.
Merchants already hire ninja to do stuff for them; it's one of the ninja villages' primary means of income. A business with a normal loan will not be able to undercut his competition reliably. The end goal of the ME plan is to have so many monopolies that eventually we can arbitrarily set the price of any good we want, within reason of course. Monopolies make an obscene amount of money and without any form of regulation (yay feudal tech level) we shouldn't have to worry about our stranglehold being disrupted by any political powers in play until we have multiple large fortunes.
This avoids the risk of frequent border crossings and makes us less delivery boys, while presenting the merchants with more direct advantages in continuing to do business with us.
The Yakuza are already illegal loan sharks in MfD (our client in Yuni was trying to escape his debts/obligations to them). Large regular sums of cash from a group of angel investors is much easier to notice than a bunch of merchants starting to undercut their local rivals.
I am not sure what you mean by "more direct advantages in continuing to do business with us". Banks
need a reputation or backing of some kind for people to be willing to use them. As missing-nin, making any overt reputation that can be traced back to us harms op-sec.
I am not against the idea on principle; I just believe that it will need a lot of fleshing out if we want to make it work.
Alternatively, we might be able to do both: having a series of monopolies and banks to work with. Banks would make retrieving payment from our merchants easier; I simply did not include establishing any since it would be one more added complexity to an already complex proposal. However, if the hivemind is willing to entertain all of the rigors of creating a bank, I am interested in seeing similar constructive discussion on this topic. The more we can bounce ideas off of each other, the better.