Wow, there is a lot of questions to be answered here!
First, 5 watts of RF of a given frequency from one radio will talk as far as 5 watts of RF from any radio on the same frequency, ALL other factors being equal. The differences come in receiver sensitivity, antennas, location, height and atmospheric conditions. When you are talking repeaters/bases, you are also talking about another radio in the loop, and that is how real range is achieved with handheld VHF-UHF radios. Nothing else will replace these.
As to the question of whether you should get VHF, UHF, or higher radios, that comes down to what you are going to use the radios for, and where. Remember, all radio frequency is part of the greater electromagnetic spectrum, SO, the lower you go in frequency the more RF acts like sound, and the higher the more it acts like light, easy right?
So, for use inside of buildings, where you want the signal to bounce around, use UHF+, for the great outdoors, and generally more range, VHF. So where will MOST of your usage occur?
Once you answer that question, it comes down to what you are going to use the radios for. It is impossible to beat the ham bands for more communications, as long as you are willing to NEVER use it for business, as this is illegal and will get you busted ASAP and two, willing to study and test to be a ham!
IF you are not, I would recommend either GMRS, MURS, or perhaps one of the other business services. But that is going to cost more and provide less coverage then Ham!
As to radios, I would get some used Motorolas and save your money. JT1000's can be had for $250 or less and are keypad or computer programmable. Old Maxtrac mobile/bases can be had for $100, or less!
I have to run off to bed, but let's talk more about this! : D
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