The two configurations are identical in principle, the only difference being the value of the equivalent inductance L=L1+L2+2M, where M is the mutual inductance.
Depending on whether the series connection is normal or bucking, M is positive or negative. In the latter case, the inductance is much lower, favoring higher frequencies and leading to the possibility of resonance at certain frequencies of the square-wave signal spectrum. Moreover, operation is considerably altered between the two cases, as the parasitic capacitances of the transistor, diodes and windings no longer have the same relative impedance to that of the equivalent inductance. The 2 circuits can therefore behave completely differently, so comparing them is of little relevance.
The force between the 2 coils is attractive in the 1st case and repulsive in the second, but this is only a mutual influence of the charges circulating in the two coils. As far as the magnetic field is concerned, we can't say there's any “compression”: there is a simple superposition of the fields and the forces are only on the charges.
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