If a food truck operator has a solid business model and a competitive product, a bank will provide a loan for the ‘young, cash-strapped individuals’ needing money to secure the licenses & permits for a food truck in any city. I imagine those licenses are for one year. So to answer your question of how Boston lands at $17,066, I would look at the bigger picture of the operation. For starters, compare the cost of those fees with the average cost of a retail space in Greater Boston for a small retail business—to be located downtown or in the Back Bay, $1,450/month would be highway robbery!
Say you have a food truck that sells ‘product x’ for an average of $10–a reasonable guesstimate compared to what I’ve seen people spend on a meal from food trucks. Some food trucks may serve as many as 50 people per hour during peak hours, which may realistically translate to 200 patrons per day buying Product X. That’s $2,000/day of money coming in, or $10,000/week if the food truck is a weekday only operation. That means under the right circumstances, the food truck could bring in anywhere from $250k-$500k per year in my fantasy scenario. Pay 25% off the top for expenses like value of merchandise, upkeep, marketing, etc ($62,500-$125,000) and another $40k/year to your 3 employees ($120,000). That leaves you with $67,500-$317,500 to draw from before you have to pay next year’s permits/license fee ($17,066).
If a food truck is selling product x and sales are forecast on the middle range to high end, I think Boston’s relatively high fees are worth it for a savvy food truck operator. Boston means business: if you don’t know what you’re doing, then get some experience first to build confidence before taking the risk.