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Site Update?

I'm trying to get the details worked out with a couple of hosting companies that seem to offer us the best package moving forward. I have been held up by some unforeseen business trips and unexpected work related items that have me working significant amounts of overtime lately. Our goal is still to try and transition by the end of the summer. We don't want the site going down or there being hiccups while we are still in driving season. We see a bit of a decline in site traffic towards the end of summer/fall time frame so we figured if we do run into a hiccup with the transition that would be the best time for it to happen.