Yeah I think the raised bed approach is definitely the way to go for your tomatoes. We built two last spring and the difference was night and day compared to the in-ground ones. The soil warms up faster, drainage is better, and we had way fewer pest issues. Just make sure you use untreated cedar or redwood for the frame — the treated lumber can leach chemicals into the soil. Also, don't skimp on the soil mix. We did a blend of topsoil, compost, and perlite and everything just took off. Mulch heavily on top to keep moisture in. The only thing I'd do differently is add drip irrigation from the start instead of hand watering every day. Saved so much time once we finally installed it. Let me know if you want me to send you the plans we used.

Oh and one more thing — stagger your planting dates by two weeks so you get a continuous harvest instead of everything ripening at once. We learned that the hard way when we had forty pounds of tomatoes in one week and couldn't give them away fast enough.