Hope this turns out to be right, but when you evacuate and charge it back up again, just think through the process very carefully and make sure there's no opportunity for introducing any air. Some of your described behavior lines up with that of a system with "noncondensibles", the most frequent we run into being air or nitrogen, and occasionally volatile oils used in manufacturing (more on that later). It takes up space in the beat exchanger, making it effectively too small to reject the heat and spiking the high side pressure. An easy way to screen for this is to let it sit for a while until the system equalizes and reaches ambient temperature, and then check the pressure. Both sides should be equal and line up within a couple degrees of the saturation pressure associated with the ambient temperature for R134a (you're looking for the pressure at which ambient lines up with the boiling point). Danfoss Ref Tools or Bitzer Refrigerant Ruler are both good, ad-free smartphone apps that will easily show you that association.
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I've read through the thread pretty thoroughly and it sounds like you're doing everything right, just wanted to put this out there in case there's something not coming through in the text.
RE: volatile oils - I remember one time we were having a heck of a time pulling systems down to vacuum before charge and it turned out that the condenser shop was using mineral spirits in their process and they just had to be exposed to the vacuum pump for a really long time to evaporate. I don't recall if it would pull down and then climb back up as if there was a leak, or if it would just not pull down. But if you have the time at the shop, it might be worth vac'ing, then sitting overnight and vac'ing some more before charging it.