Depends on your definition of handheld.? There are plenty of guides available to run fldigi on a pi.? The radio, battery, pi, and ancillary cables and connections would be a handful for all but Fezzik (or any other giant) to hold in hand, but I don't see why you couldn't put all of that in anything from a backpack to a wheelbarrow and use a phone or tablet to VNC into the pi.? This is assuming you have an antenna figured out.? You need some space between the BITX and pi to keep RF from killing the pi's wifi but not much.? I have my ?BITX in an unshielded plastic case less than a foot away from a Pi3 that I can keep a constant wifi VNC session open to.
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