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Never upgrade your starting garage until you have multiple other garages at 5 slots. Upgrading your starting garage is the most expensive thing you can do in the game.
Now I have to pay 7500 a day
Best deal ever.
drive a provided truck poorly and hit a telephone pole and you'll get a worse reward and score, if you do the same with a truck you own enjoy the insane repair costs, i've paid more than $25k for repairs after one particularly drunken delivery before.
The most economically sound course is to keep saving until the bank offers the largest loan (400K). Then take that loan and either expand your existing garage or buy a second one. Buy a truck for yourself and another for an employee and hire your first employee.
Once you have your own truck you'll be almost doubling your income from Freight Jobs (Freight Jobs actually pay double but you'll have to pay for your own expenses out of that) and will be having no problems whatsoever covering the daily interest plus plenty left over for savings and covering any initial losses from your employee (until he levels up more he won't earn you much and tends to dead-head back home more often).
Either way, it's your game, play it how ever you like. No matter what you do it won't be long before you're making more money than you'll ever know what to do with. Some paths will just get you to that point a little sooner than others :).