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This really depents on how the exisitng garage is framed, but in most cases is could be possible. Would entail a new header and side studs, then then siding & trim.
The biggest issue we run into is not having enough black dirt (quality soil) on on hand. Trucking in more soil can add thousands of dollars, and it's not often evident at the start of construction or remodeling.
Drainage is a common issue that clients don't anticipate.
DuraShield by StreetBond, which is a Quest Construction Building product will solve your issue with driveway cracks. This product will need to be applied every 5yrs or so, depending on the weather conditions in your area.
Patrick McDonald
LaGrange,GA
You night try Pine straw instead of wood mulch. It's less prone to washing.