Nice project Wolf, and a good result for an 8" 2-way with 5 components!
I hope you don't mind me adding this in here. I was looking at all the squiggly lines trying to figure out which was which, and getting confused that your far field right response looks too similar to the near field left plot. Anyway, I found the file names that you posted which cleared a few things up for me. This isn't really a criticism of your project, just something I decided to play around with because I can, and you had provided a lot of squiggly lines to play with.
It strikes me as odd that you took a nearfield measurement, but then didn't use it in your simulation, it appears that a far field "blended" plot was used in simulation, IMO this makes it hard to judge how much BSD you are adding in, but I'm sure you have your reasons and methods that work for you. I had a half hour to kill, so I traced your data with this neat online tool and loaded it into SoundEasy. I merged your nearfield data with a BSC sim with the far field data at 600Hz, so you can see the low end response a lot better. To be clear, I checked that the transfer function and impedance is a match, the only real difference here is the woofer frequency response data (I used the left speaker data).

I think what you have here is very good, especially the fact that there is a bit of a dip in the 3kHz region, this will help compensate for the "directivity bloom" from crossing a 8" woofer to a 1" tweeter. There is a bit of a lump in the response at 1kHz that doesn't show up really in your response simulation above, but it is evident in the filter transfer function. I think you made good compromises here, as you'd have to go over the 5 component rule to improve this further IMO.
For reference, this is the raw woofer "merged" response:

I hope you don't mind me adding this in here. I was looking at all the squiggly lines trying to figure out which was which, and getting confused that your far field right response looks too similar to the near field left plot. Anyway, I found the file names that you posted which cleared a few things up for me. This isn't really a criticism of your project, just something I decided to play around with because I can, and you had provided a lot of squiggly lines to play with.
It strikes me as odd that you took a nearfield measurement, but then didn't use it in your simulation, it appears that a far field "blended" plot was used in simulation, IMO this makes it hard to judge how much BSD you are adding in, but I'm sure you have your reasons and methods that work for you. I had a half hour to kill, so I traced your data with this neat online tool and loaded it into SoundEasy. I merged your nearfield data with a BSC sim with the far field data at 600Hz, so you can see the low end response a lot better. To be clear, I checked that the transfer function and impedance is a match, the only real difference here is the woofer frequency response data (I used the left speaker data).
I think what you have here is very good, especially the fact that there is a bit of a dip in the 3kHz region, this will help compensate for the "directivity bloom" from crossing a 8" woofer to a 1" tweeter. There is a bit of a lump in the response at 1kHz that doesn't show up really in your response simulation above, but it is evident in the filter transfer function. I think you made good compromises here, as you'd have to go over the 5 component rule to improve this further IMO.
For reference, this is the raw woofer "merged" response:
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