deep repointing and mortar guns

When it stops raining I'm going to repoint my kitchen wall. I've never tackled this before, so would be grateful for advice. It's in pretty bad nick - in at least one place I can put my 6 inch pointing trowel all the way in - and that's before I've put my chisel and angle grinder to work. How do I fill deep holes like that? Just keep shoving mortar in? Would a mortar gun make it easier to fill a deep joint from the back?? I've been looking at two, the Point Master (claims to not separate water in mix by using hand pressure), and the Pro Point gun (comes with a deep injecting mortar nozzle).

Also there is a lot of condensation/damp in the kitchen. Is it worth putting some water repellent on the brickwork once it's finished? Or is there anything else I can diy to improve things?
cheers
Peter

Hi, Peter.
You do have a problem.
use a strong mortar mix, 5-1 and force the slightly dry mix right in to the joints until you can get no more in.
Use a pointing trowel and a plasterers hawk to load the compo.
hold the hawk at the level of the bottom of the joint to be filled and push small amounts in until full, and then point up the surface.
Alan D.

As chessspy says but:

I found a pointing trowel to be pretty useless for this. I cut a block of wood, about 8mm thick, inch wide. I put the mortar on the hawk, gather it together with the trowel, then push it into the hole with the block of wood.

The pointmaster is excellent for filling deep joints, and good for quick pointing in general. Just make sure the mortar has plastiser in and is nice and creamy.

Penetrating dampness would most likely be due to poor mortar joints, and specifically the weathering face. Sort this out, and no need for additional water repellant.

If the kitchen suffers condensation dampness, then that is nothing to do with the brickwork, and that needs a different solution