I felt my ears burning so I logged on...
Wood in particular will really put a lot of weight on the step edge... bad news.
You do need to fix this.
We just did a Floatlift for the OSO Gladiator. The lift has aluminum/rubber bunks that have some flex. They won't put as much weight on the step edge as straight lumber. We are in the process of building wedges for the boat that put some of the weight from the void back on the bunk/hull to take weight off of the step edge.
Pic is shown to illustrate why we want to fill the gap.
First- Step boats are a PITA in the lift business. Fit/operation will never be perfect.
The operator MUST remember to have the lift in it's lowest position before backing off the rack, or the step mods will catch on the back side of the bunk and likely gouge or upset the gel on the back of the step.
This is the operator's responsibility.
As far as loading goes... yes this is tough with step boats.
Take a specific reference when the boat is properly positioned. You must stop there before really raising the lift, or again, you can chip a step.
Generally, a guide on will line up with a part of your boat to give you a ref, or take a piece of tape and stick it to the boat where it lines up with a fixed point... get it?? Let me know if you need more clarification.
With regard to your particular lift....
Myco makes a wonderful cradle for the old school cable lifts. Pricy but good. But then again you spent a load on that boat anyway...
If you don't want to go Myco.. I can help you out with aluminum bunks and wedges, just like the OSO boat. Or get you in touch with someone locally to cut and chop your wood....
Don't hesitate to give me a call.
Sunstream Boat Lifts