pretty brave tackling the merrimac as your first solo endevour. The merrimac is alot of work with or without a mate. If your not looking out for yahoos your navigating the twisting channel or battling a good rip. Lets remember your out there for fun and you want more than anything for your kid to have fun. If he doesn't, then you will most likely lose a fishing buddy. Stress = no fun
If I were you, i'd take the trek up to Gloucester and launch there. Way less stress and the fishing is..... well....... there are no fish in gloucester we all know that

. In fact I don't have to be you... I do this now
I grew up in Gloucester and have transplanted to Groveland. First year here I fished out of the merrimac hard. And after witness to 3 shoving matches, with and infinite amount of potentials at the ramp I decided the 45 minute trek was worth it. I'll venture over there a couple times of year but i'd rather have fun
Just my two cents.