I assume this is at least a 4 layers board, right?
There are a couple of things that I see at first glance. First one is that you should place the intra-pair length-matching meanders as close as possible to where the length mismatch occurs. In your case you have a huge length mismatch at the top connector, so you should adjust the length of the shortest trace in the pair as close as possible to the connector exit. In your case it would be better to use a large meander rather than several small ones to compensate the length as quickly as possible.
Also, as you are forced to have your pairs uncoupled for quite a bit of length, you should aim for a loosely coupled pair geometry. I mean, you can get a 100 ohm differential impedane with two tightly coupled 70 ohm traces, or you can get it with two very loosely coupled 50-ish ohm traces. In your case, the latter would be better, making your layout more insensitive to the uncoupling that occurs near the top connector. This also helps with via design. Tightly coupled pairs require good via design to avoid discontinuities (antipad and pad diameters and such), while loosely coupled are more insensitive and will do fine with more carelessly designed vias. You'll have to increase the antipad size for your vias anyway to reduce their stray capacitance and minimize impedance discontinuities.
Also, every time you switch layers AND reference plane (in your case you switch your pairs from top to bottom, so there's a reference plane change unless you're using a 2 layer board which you shoudn't) you have to add ground stitching vias near the layer switching vias to provide a good path for the return currents.
Finally, sometimes you need to create voids in the reference plane immediately below connector or component pads if they are much wider than the high speed traces to reduce the parasitic capacitance and minimice discontinuities. This becomes more critical the higher in Gbps you go.
As long as you're not going past ~10Gbps per lane it should be """"relatively"""" easy to get working. Past that and you'll have to take into account prepreg weavings, copper roughness, your layer transitions no longer work as "lumped" discontinuities and many other aspects.