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Sure, you can always try it without an amp first and then add it later. It's likely that things will work, but you'll be that much closer to the edge of failure (the so-called "digital cliff"). The amp merely give you a bigger buffer so that natural signal fluctuations (which inevitably will occur) do not turn into visible channel drop-outs or video break-ups.
The other way to look it is that if you know something will help (and I think the amp will help), and it doesn't cost that much, why not just do it right on the first try. I'd rather save myself the trouble of going up on the roof a second time to mess with cables, connectors, masts, and making everything tidy again.
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