I appreciate everyone supplying links and info. Thinking about this has prompted me to learn a lot more about APRS than I ever thought I would. Oddly enough, when I was first licensed I thought APRS was kinda dumb, to be honest. Then, a couple of years ago I bought an FT2D mainly just to say I had C4FM capability, not even knowing or caring it was APRS capable...
A point of clarification - I said the nearest I-Gate was 25 miles away, but I should have said that the nearest digipeater is about 25 miles away. Testing so far has been on the handheld with 5 watts, so not an ideal setup; but another thing to note is that there is no traffic on 144.390, so not only am I not hitting any digipeaters, I'm not receiving any, either. Thus why I'm wondering if my proposed setup would be able to get "out" or if I'm creating an island, so to speak. I think the only way to know the truth here is to try a mock up to see what my proposed setup would be capable of.