I bought a compressor powered vacuum brake bleeding kit about a year or two ago, but using it on my bikes and my old cars it has been really shit. I only use it for complete fluid changes, not just for general bleeding of air bubbles....
Does your softy have abs...?
No, sorry - 1996 evo heritage softail.
I had the same problem with mine, Just crack the bleeder enough to start the fluid moving while your topping up or have a buddy topping the resevoir.
Try a Dyson. LOL