Signal strength will not be a problem... they'll be plenty of it. :-)
SONAR's external insert feature woks ok with analog gear because, well... it's not neccesary.
SONAR's basic DC will sync up an analog round trip REAMP process... it is no different than any other overdub.
With a digital processor, such as we are speaking of... SONAR's external insert feature might work. It is the latency in the outboard digital processor that needs to be compensated for.
In a real world... the latency that a digital processor exhibits is usually conditional to the task the digital processor is working on.
SONAR only measures one instance and then when the latency on the external digital processor changes you are in the weeds.
It's just another half baked... not really thought through, doesn't really work as you need it to, bullet point feature that frustrates long time Cakewalk customers. The problem is caused by a condition outside SONAR but the solution is inside SONAR. It's not addressed very often, and so most folks are left to discover for themselves that they are arbitrarily out of sync and still have to resort to manual alignment.
I only use external inserts for analog so I never use SONAR's external insert feature or get frustrated by it.
If you are using a GP-100 digital effects unit... you might want to just do a ping for each patch and slide it manually. You'll have to figure that out. It depends on how much digital work you ask the GP-100 to do and how much latency it requires for any given patch.
The level's thing will be real obvious... like almost immediately. :-)
all the best,
mike