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A few updates from last night's work: I tried bouncing my full weight on the outboard leg in trailer mode. No detectable flex; felt very solid. I did a deeper examination of core at the top of the transom, using a longer, larger-diameter drill bit. I did find solid, dry-seeming balsa all the...

Area with dull-sounding hammer blows.

Chain hoist to lift main outboard. 1000lb strap, secured to 3 laminated 2x4s spanning 4 ceiling joists, and to an adjacent 6x6 strutting beam.

Fuel tanks removed and tank area cleaned.

Area behind starboard fuel tank; dull-sounding hammer blows in centre of this area.

Drillbit shavings from exploratory holes down into the transom from the top. Wet, rotten balsa core from upper 2" below the transom cap (right) and dry balsa from ~3" below the transom cap (left).

Thanks Clay - that's a good option to consider now (before I dig any further and eliminate that possibility). I certainly haven't been noticing any flex or mushiness to the transom or elsewhere - I'll do a bit more careful checking to that end no matter which direction I go. My initial repair...

My next step was to evaluate how far along the transom top there was wet wooden core. I drilled a series of vertical test holes through the top of the transom, from left to right. While the worst rot was centred around the main motor mount, the core all the way along had at least some moisture...

My initial take was one of only moderate concern. While I could see core through the crack (bad), it appeared to be something other than wood (good?). It was a light-coloured material, that I could gouge out with a screwdriver blade. Foam? That would be good - perhaps I could get away with a gap...

I've discovered a crack in the fibreglass beneath the black plastic transom cap on my 2004 22 Cruiser. On removing the cap and inspecting further, it's clear that water's gotten into the wooden transom core. I'll investigate further, and plan a repair. While it's a disappointing discovery for...

Starboard side transom, cap removed.

Close-up of rotten wood picked out from gap in transom fibreglass.

Transom beneath main motor mount, with cap removed. Rotten wood picked out for investigation.

Port side transom, cap removed, below kicker bracket.

Port side transom, cap removed.

Transom cap removed.

Fibreglass skins separated beneath black plastic transom cap, exposing core.

Thanks all - this is all very helpful input. Has me thinking longer-term; my outboard's original to the boat, and will at some future point require replacement. I'll assume/hope that any new steering system would still be in good shape by the time I swap motors. Is there any consideration for...