and, finally, a direct response to the question asked!
What a hoot, fellers, the poor guy asks
WHERE
to train, having already made, and clearly announced, the decision
Whether
to train, and in "answer" to his question gets reams of responses pro and con the Whether issue. It wasn't the question!!!
HIO vs FL: I've trained in both environments; even raised my family in the HIO area, and did broadcast-station traffic-watch flying for a couple of years. HIO has a large, and reasonably well-organized, school; FL has several that are bigger and cheaper. Oregon has no sales tax (+), only income tax, and CFI's have little income to tax! FL has sales tax, not as beneficial for CFI's.
Weather: I suspect you can get 10-20% more flying done in FL than OR. Except for its brief summer, HIO gets rain, drizzle, and heavy fog a lot of the time. FL is merely hot and muggy for 6 months+ a year.
Mountain Flying: Not much difference: HIO is hardly mountainous terrain, and the coastal hills rarely get over 2-3000' MSL, so density altitude is a non-issue. Trans-Cascades flights are nearly always via the Columbia River Gorge; that is, at sea level!! So all we can say is Oregon is more scenic. (The 5 major volcanoes on the skyline DO enhance positional awareness!).
Economics: OR job opportunities are seriously downgraded by the long-term slump in timber industries, have been crying poor for years. So there are undoubtedly many more jobs in FL, where there is a constant influx of refugee heli-training candidates from the rest of the world. (As of 2001 or so, over 22% of USA CFI certificates were earned in FL--most of them by visiting pilots-in-training.)
Culture: Portland/Hillsboro scores pretty well for the arts, and for the intellectual skills of its residents. FL . . . well, quite depressing; FL is seriously lacking.
Where would I raise my family? OR, without a doubt. Better school system, sometimes-enlightened state government, general progressive attitude. FL, by contrast, seems to be dedicated to coasting on the immigrant influx of retirees from New York City, so education levies are rare and inadequate!
So it goes, trying to figure out how to structure our lives, studying, weighing, making lists, trying to be rational--and then, ultimately, some employer or government somewhere flips a coin and all our efforts are for naught.