OffRoaderX

I would respectfully disagree with my colleague from Montana on #4 - I would take elevation/antenna-hight above ground over power any day.
UNLESS he meant electrical power to run the thing? In that case, yah, he right.

The firmware updater runs only on Windows..  It *might* run via Parallels on your Mac.. But, it might not.. and I dont recall, but you may also be able to do it via the ODMaster app...
But... are you really sure you even need the firmware update? I usually avoid firmware updates unless it fixes something I actually care about.

Why?

For comparison you could look at one of the pre-programmed repeater channels 23-30 You could key up and if you have it wrong it wont matter/wont hurt anything On a GMRS repeater if the frequency given is 462.xx then it will always be +5 It looks like you haven't added the recieve-tone, but that is optional anyway, and for a beginner/to reduce potential mistakes i would not bother with it yet It all looks right but the only way to know for sure is to try it.. and remember, if it's not right, it doesn't matter/nothing is going to break/no airplanes will drop from the sky.

The offset is 462.700 +5Mhz = 467.700 - thats what you are seeing on the screen when you transmit. Because it's a GMRS radio, you dont have to worry about entering the offset because it's all automatic.
The radio is working 100% as it should.  If people aren't hearing you it is because you are either not in range of the repeater (just because you can hear it does not mean you cant hit/use it from your radio), you put in the wrong tone, or did something else wrong. 

Dont mess with it - 2.02:1 is plenty good enough.

Thats exactly how its supposed to look... So, you do not have  File|Edit|View|Radio  menu options in the far, upper-left of your screen? (SCREEN, not WINDOW) ?
Like this?:
 

You can enter Dealer Mode in the standard software by adding a couple of letters to your program shortcut when you run it - I dont remember what it is but you can search for it here - it's something like "/D" after the .EXE .. Once in dealer mode you can enable CW-ID and a bunch of other stuff.  Warning: Dont change something if you dont know what it is..
But no sexy voice option.

Assuming those are the correct tones (I didnt verify), then, yes..  You can simplify even more by omitting the RX tone, which is optional.

Those tones sound familiar...
My guess is that you have the tones backwards, OR it's actually working the way it is supposed to.. Be sure to enter the 271 on your radio's TX and 073 on your radio's RX.. Note that these are DCS/DPL tones, not CTCSS tones so make sure you are putting them in the right place (consult the manual).
Leave the RX (73) out for troubleshooting.. If you enter the TX (271) and can hit the repeater, then you should be good. When you enter the RX (73) then you should then ONLY hear transmissions from that repeater and nothing else - this is optional.