Hi fmulligun,
No expert here, I'm just now educating myself with hours of online reading on the subject, but here's my "educated" guess...since it's in a container, I would err on the side of too much vs. too little, as the drainage holes should take care of the regulation for you. Too much water, the holes will eliminate the excess. Too little, the plant will let you know, by either wilting or not growing . An additional note, WATCH THOSE HOLES, make sure they're doing their job....if you can make a hole in the soil with your finger and the hole fills with water, the drainage holes are clogged somehow, or not large enough. I have two in 5 gallon containers up on bricks in my yard. After a rain, I noticed that one was flooded. I drilled more larger holes, and sloshed around the edge of the soil with a screwdriver to stir it up a bit, just before a heavy rain fell last night. Today, soil is drained, but my 'mater would have rotted had I not checked.
They say that tomatoes in the ground should be watered deeply once a week, but more frequently for containers due to the rapid evaporation of the decreased amount of soil. I think you'll be fine, don't sweat the amounts. Those who have been doing this for years will tell you one way or another, listen to them, not me.

Yeah so far I have overwatered and under watered. The container was just to small and had no stability. I am hoping the bigger container will allow for more error.

If you are unsure of your ability to tell if the pot is too wet or too dry, go buy a moisture meter. I have seen then for under $10.00 and some as low as $5.00 or $6.00. Since you have already invested in the plant, soil and pots, it is not too much more to insure you correctly take care of all you have already invested.

Bets

Here is a link that might be useful: Garden Moisture Meters

Container should have easily draining soil.I water my containers til the water is pouring out the drain holes wait a few minutes and water the same way again I don't thnk you will have a overwatering problem in your zone. It helps to mulch also as it slows water evaporation.