Did Caesar borrow to gain office, pay debts through war, and then borrow again for higher office?
Short answerBroadly yes, with significant financial backers helping him sustain that cycle.
NotesThe answer broadly accepts the proposed cycle of borrowing to gain office and using success in war to repay debts. It also stresses Caesar's substantial financial backers. Their support belongs alongside his campaigning when considering how he could sustain that career.