I string a good deal of nat. gut.
I would string it 2 piece as well. The string gets handled less that way, and also start the cross strings top down no matter what racquet it is, as the top cross strings will be the freshest and when you get to bottom it becomes handled more as most of the hitting is center to top.
Also if you have a diablo, use it, and if you need to pull the same string twice, then wrap the string around the diablo a second time so the tension head grabs in a different spot.
Be sure to not only weave one ahead, but also try to pull most of the slack of the cross string one ahead as well so the string gets less wear.
I also just pull the knots tight with fingers only, as if you pull too tight with pliers you can snap or weaken the string.
If you are concerned of blocked holes, then place a scrap string under the main that skips the hole on outside of frame as that way you can either lift up or pull down on the scrap string to open the grommet hole.
Biggest issue is take a little extra time so you do not accidentally kink the string