If the Watchtower REALLY believed in the life saving nature of the witness work they would be on an emergency basis.
I think you are going a little too extreme in your expectation to preach. Christians were given a commission to preach but it was left up to the individual as to how much they were to do it. People have families, jobs, etc... Jesus also said later on that the preachers would have to carry a coin purse latter on because of the inhospitality they would eventually find.
The pioneer arrangement, missionary arrangement and other arrangements are different levels of public preaching that individuals can avail themselves to according to their circumstances. IMHO the witnesses have taken this commission to preach more seriously than other churches.
If they took it seriously they would discourage people from spending money on luxuries, - cruises, vacation homes, luxury automobiles, . Everyone would REALLY be content with sustenance and covering.
I think they do this all the time. As for being content with sustenance and covering, what compromises this is a individual choice.Christ wasn't setting up a little Nazi state.
They never took it seriously.
I think they are not as effective as they could be. They us only one primary method of mass media, the printed page ( and to a much lesser extent, the internet) . As IP_SEC mentioned, they have Radio, TV, greater internet use, ads in other magazines available to them, etc... but they don't really avail themselves to these other forms. (the media terms for this is called horizontal integration and symbiosis)