Hi Mike
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Regardless of what obstacles you may perceive, you should, by all means- proceed. Ham radio is made all the more fun by overcoming them.
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You didn't say (or did I miss it?) where you are located that places you several hundred feet below average? That can mean a lot- as in at the bottom of a steep coulee, cut bluff- or like me, surrounded by mountains that towering to 14,000 feet.... or by gentle rolling eastern hilly plains-- all are going to effect the answers you'll get or the solutions you might need.
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Knowing no more than what you've said, I'd say you've nothing to worry about- especially if its VHF repeaters you're interested in. Probably handheld radio maybe a disappointment, but a home station of 25 watts and an small outdoor beam antenna will cover a suprising range, even at a less than optimum location.
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And keep in mind, there is plenty of other aspects to the hobby beside V/UHF repeaters. I could fill your head with ideas, Cowboy! ...
but I'll just leave you with a "Good Luck!"
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.........................CF
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