If you ask anyone with an apprentice, the trick is to order extra EMT.

The offsets are not too hard. Use the 30 deg bends, so for a 4" offset make marks on the conduit 8" apart.  The bender handle will be plumb to your floor at 30 deg.  
Use the same mark on the bender for both bends.  I often make the offset bends with the bender handle on the floor and the head up, using arm pressure on the conduit.  Then eyeball the offset to keep from dog legging it.

The 90s need a lot of foot pressure to keep from wrinkling the conduit.

Ream/smooth the cuts you make to remove any burrs.

Rain tight fittings are appropriate for an outdoor install.

I can do this stuff in my sleep, but not very good at explanations.  Fire away with any more questions.

Have you considered using the gray pvc conduit? You can heat it with a heat gun and bend it by hand. Never done it myself, but it should be easier than bending emt.

You should see someone learning how to use a hydraulic bender.

All it does is let them f-up faster.

There's an app for offset and angles   I've heard from sparkys on the job it's easiest to do a 30/30 bend.  I could be wrong. But he did say there is an app for it lol

You don't need an app to do offsets at 30/30. That's the thing, use a multiplier of 2.  8" offset gets you 2 bends at 16"

Maybe this will help... maybe not.

PIPE BENDING ... 101
(basic version)

"How do I bend pipe?"

You really only need to know a few techniques in order to bend well enough for what most people need to do ...

*Bend a 90 degree bend
    at a "certain" place.
*Bend a 90 degree bend
     up to a "certain" height.
*Offset the pipe to either run up or down to a different level.

There are 2 marks on a pipe bender that you will need to use ;
    An "arrow" and a "star" .
Remember ...
"Shoot an arrow HIGH up",  Or
"Locate WHERE you are, using a star."

So ...
To bend a 90 degree bend up to a certain height.
Bending a 90 up obviously raises the very end of the pipe up off the ground. How high, is up to you depending on how much of the pipe is in "front" of the bender and, also (what is called) "takeup". For 1" EMT, the takeup is 8". ((for 3/4" it is 6", and for 1/2" it is 5")
So, say you want to bend a 12" 90.  Mark the pipe @ 4", put the mark on the ARROW, and bend the 90.  4 + 8 = 12. Easy.
The end of the pipe will now be pointing up and the end will be exactly 12" above floor level.
Use foot pressure on the heel of the bender much more than arm strength AND keep the pipe from rising off the floor. That will make your bends correct and consistent.

Next. How to "locate" a 90 along a pipe. Note that you always locate the "back" of a 90. If your pipe runs along the floor and has to turn up exactly on a wall, it is the back of the 90 (against the wall) that is important.
Forget about how high the 90 is.
Your pipe runs along the floor and has to turn up (for example) 62" away.
Mark your pipe @ 62" and put the star on your mark. Bend a 90 and the back of the pipe will end up at exactly 62" along the pipe.

Offsets are easy, too.
Always use 30 degree bends.
  ... It is easier to pull the wire, the bender handle is vertical when you reach 30 degrees, and the "multiplier" is two. What this means is that if you want your pipe to offset up ...for example ... 11",  you put two marks on the pipe 22" apart.
Bend one 30deg bend, slide the bender back 22" to your other mark, "rotate"  the pipe 180 degrees so that your 1st bend is now facing down, and bend the 2nd 30deg bend up. If you were careful, the bottom of the end of the pipe will now be level AND 11" above the floor.  
But if you need to,  bend a bit more or less to adjust.

Stay safe

Post a picture of what you bent and where you are trying to install it.