Best practice for tool length offsets?

Hi, I'm new to this so please forgive the rather basic question...

What is the best practice for tool length offsets?

Both the CAM software and LinuxCNC have tool tables. Do I need to program both? Do they have to be identical? Could I have the nominal length in the CAM software and the precise length in the LinuxCNC tool table?

When I generate code from the CAM software should I do tool compensation in the CAM software or allow LinuxCNC to do it?

Since the answer is likely to be... it depends... here is some detail about my specific case:

I only have manual tool change. I've seen it recommended to split the code into a file for each tool. I can see how that would work allowing Z touch off for each tool, but I'd really like to try to get the tool changes working in a single program.

I use ER collets but have several Easychange holders, so I should be able to measure each tool during setup. I think it will be easiest to enter the precise lengths into the LinuxCNC tool table. I think this means that when doing the CAM programming I should select "tool compensation - in controller". In that case, perhaps it doesn't matter what lengths are set in the CAM software, they will only be used for simulation? Please confirm.

I've seen some threads where people used a custom subroutine for the tool change that touched the tool onto a probe to automatically update the tool table. This is also of interest.

What do you guys recommend?

See if you can find a marble bench offcut from a sink and drill a hole in it with a broach drill bit big enough for your tool shank to fit through. How to videos on YouTube of course!
Then get a Digital Height gauge and measure each tool and enter the height into the tool table. This is how Tormach do it for their TTS system which is similar. I adopted the same approach and bought a Tormach marble plate from little machine shop for my TTS tools.

Then grab a cheap Chinese 3D probe and adopt QTdragon_HD (requires 1080p monitor). You can then probe to the material height near a corner, then locate the corner (or boss or pocket) with the probe.. Swap the probe for a milling cutter and you are good to go. 

As far as doing it in CAM, F360 will either do it in CAM or on the machine. Doing it on the machine you leave the tool diameter blank in LCNC and F360 will use it for offsets. Alternatively, quick and dirty, just tweak your tool diameter in F360  and repost.

Good luck!