Well to answer the last question - yes a decent dev will be able to MAKE the frontend and backend. Designing the front end is a different story...
The advice I give in these situations is to sell the product before you have anything. See if your boss would buy it - tell him you've found a great solution which does x, and y, and costs $Z per month. Don't underprice your offering - if it's good, and it solves a real problem, then people will be willing to pay a decent amount for it. I don't know what prices you were thinking of, but you could tell him it costs $50 a month.
If that's too high for him, ask if you could get it down to $30 if he'd be willing to pay for it.
Before you pay a developer, do a front end design - make it look nice (I'd steal someone elses design), and have it explain what your service does. Then set up adwords or advertise your site, and see if anyone clicks to buy the thing.
If people are clicking to try what you've got then you might have a product -otherwise you've just saved yourself a shit load of money by not building the whole friggin thing.
Lou
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