Steve,

One of our customers they had similar problem with press-fit connector.   I
don't think it was right angle though.

Anyway they asked us to prepare a backing plate (in this case we drilled a
0.125" mat'l with a bit larger holes than finished brd holes) that they can
use it as support under the brd.  You can have more thickness by stacking
such plates to create clearance for components.  And after that they used a
hand press to install the connector.  They used metal plate over the
connector to evently distribute the pressure.

Hope this helps.

Rush
Accurate Engg
818-768-3919

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