You may lose autofocus on those body / lens combinations, IIRC an xxxd body will autofocus down to f5.6, when you add a converter on you lose a stop (so an f5.6 lens becomes an f6.3 lens). Worth checking before you chuck a load of money at it.
I don't think that the Canon 1.4x will work with EF-S lenses, so your 55-250mm will be a no-go. The Kenko should fit fine but I have never tried this combo. The Kenko worked well with my 70-200mm F/4L & 7D.
I have a D200 and wondered if a TC would give me good results with my recently purchased Sigma 70-300mm. I'm only just getting used to the lens itself and already find it troublesome in less than good sunshine.
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