Well, first you will need to know what you are ALLOWED to do.
If it is a totally private lake that is one thing, if it is or borders a designated wet land that is something else.
If it has seasonal lows you can probably do some work when the level is down, but beware dredging regulations.
Here are a few disjoint numbers and guidelines you can mess with.
I/O "runabouts" up to about 25 ft probably draw 3 ft., maybe 3 1/2 ft when the drive unit is fully down.
I'll go out on a limb here and suggest that 25ft is just about the practical limit for trailering behind a 3/4 ton truck.
It isn't the length, but the proportional depth and width - 8ft 6 in being a highway limit.
Inboard ski boats around 19 or 20 ft draw 2 ft. 18 inches or less when on a plane.
I don't DO the wake fake thang, but I suspect those draw more, since they are pretty much DESIGNED to put up big wakes they almost certainly sit low in the water.
For launching from carpeted bunks a good rule of thumb is to back in until your trailer wheel fenders are JUST under water.
At that point you may be able to float off if the ramp is at a steep enough angle, or you might need to power off if it is a gentle sloped ramp.
I don't have any numbers for this, it is an intuit thing, you go in farther or less when you recover the boat.
This usually turns out that your truck wheels stay dry, which is good.
You might be able to figure a minimum angle from this fact, i.e. truck wheels to trailer wheels when trailer wheels are just covered and truck tires are still dry - tan or sin, one or the other (-:
Sail boats,,,, could be anything, depends largely on whether they have a real keel or a fold up dagger board (-: