Having options for yourself and your guests would be nice. With 2 different boats you could accommodate a wider range of choices. The more guests and clients you have, the more advantageous this would be.
You seem to have eliminated the Adventure as an option, perhaps because of its length (too bad). The Sport is easy to transport, and maneuverable, but slower and weight limited. The Outback has a comforting initial stability for novices and good deck space but is slower and noisy. The Revo is your best all around boat, but having 2 denies you any boat options.
One important consideration -- if you're going offshore (or in heavy chop), the Revo handles and rides much better than the alternatives (except of course the Adventure), but in flat water, the difference is not as noticeable.
Perhaps a demonstration in the Outback would help in making a selection.
