I know I am putting mine in this year from the inside and it is staying there all season as I added another coat of epoxy to the bilge and it is water tight for sure. I do plan to have a float switch on the bilge pump though. Most do take theirs out after every use. But as Bondo said it does not matter too much about what side you put it in on.
I am not sure about the laws here but I am not too concerned about it since I will only be on 2 lakes and they are connected by a lock system. I will check though and see if there are any and what punishment is in place should I get caught.Make sure your state laws do not require it be out when transporting. In MN towing with the plug in is a big fine for violating the AIS laws
Screw in plugs usually go in from the outside. Rubber flip plugs go inside.
I would say the rubber expandable plugs go on the outside ( water side) of a boat Chris. The water pressure from the outside puts pressure on them to keep them sealed. Just like an industrial flapper or seal valve, pressure keeps them seated. I don't like the flip plugs especially in weedy water. There is a chance a weed will wrap around it and flip the plug open and pull it out if weeds are around the prop. I use the screw in type rubber plugs. As far as the machined threaded plugs I would think the same principle applies. I'm not a glass guy but I have never seen a screw plug from the inside. Maybe I didn't care to look.