1. How would you do it. 

I would just simply let you do it and grant you the luxury of all the hassles and failures...
 
2. In your opinion do you think its a achievable or am I wasting my time. 

That's 2 questions, but the long answer is...
  1. No
  2. Yes

 3. Or just completely crazy, and i should just turn the tools off and walk away.  

BTDT... Thicknesser is not reserved for Queenslanders' mentality. 

I'm no engineer... the closest I got was to catch these red rattlers in Victoria during the 70's,

However, (back to your stump) at the early passes there was enough "meat" to support the sides, but as it gets thinner, it will shred like pulled pork (preferably cooked... saves the blood).

May I suggest you abandon your quest for that wallet and buy a new one... then use that to amass your shekels to buy a replacement sander, as Amelia will never flash yours again.

Looking at the gnarled wood, I would suggest stabilising... flood it with CA or soak it in Earl's before maybe 1/2 thicknesser passes and then go sanding.  Maybe seal the surface and you could use some vac clamps to hold the odd shapes for sanding... ROTEX... don't get blindsided by pottzy's Bos¢h.

Failing that, start drinking out of casks... they don't need bloody coasters.
Fire up Treasures of Nadia... it'll give you inspiration, or at least take your mind off your troubles.

If your first cut is too short... Take the second cut from the longer end... LBD