Can I combine several loans to the same person into one case?

Where you advanced money repeatedly under what was really one understanding, the law looks at the relationship rather than the individual transfers, and treats the accumulated balance as one claim. Dividing it into several filings to stay beneath a jurisdictional ceiling is not permitted, and attempting it risks dismissal while also consuming the limited filing allowance you were trying to preserve. Combining them is also simply the better case: a single statement showing every advance, every repayment and one closing balance is easier for a judge to test and much harder for the other side to chip away at than four separate stories told in sequence.

Where the total sits above your ceiling, the choices are the familiar ones. You can pitch the claim at the limit and forfeit the balance, a decision that locks in the moment judgment is entered, or step up to limited civil, which tops out at $35,000 and lets lawyers appear for either side. Set the sum you would forfeit against the added expense, procedure and waiting, your own hours included, since the larger forum eats far more of them. Truly independent arrangements, made at different times on different terms with no connecting understanding, can stand as separate claims, but treat that as something to verify rather than to assume in your favour.