There are two kinds of mass, inertial & gravitational. Inertial mass tells you has resistent a particle is to motion, gravitional mass tells you hard strong gravity pulls. It was a puzzle as to why these two kinds of mass were exactly the same. It was Einstein who used this equivalence to physically conjecture General Relativity.
Mass as condensed energy just means that energy can too be the source for the gravitational field.
The weak force is a gauge field, and as particles, the force is carried by bosons, which like all bosons are massless. But this would mean that the range of weak force is infinite; experimentally this isn't true. One then suppose that the boson must carry mass. The question is where this mass comes from.
Its comes from interactions with the Higgs field; and the Higgs bosonHiggs boson is the interaction of these two fields - the Weak & the Higgs. As wikipedia puts it:
It would explain why some fundamental particles have mass when the symmetries controlling their interactions should require them to be massless, and why the weak force has a much shorter range than the electromagnetic force.
Your question is:
Wouldnt breaking open the endless "russian dolls" of matter to find the most fundamental particle which gives mass to matter be fallacious
Its not mass for ordinary particles that has been conjectured and found; but those of the weak force. Ubiquitous - yes; but not the sole source of mass.
Would it stand to reason that Energy gives mass to matter
On, the whole; and despite the Higgs boson; this is still true (or its converse).