Are there any regulations that I would need to adhere to if I wanted to bake and sell cakes online? I would only be shipping within the United States and offering the product at a premium price point.
Here are somethings I'm having a tough time trying to figure out:
Regarding the business model, I have ran a short test with Google Adwords with the offer being a monthly subscription server (i.e. Get a unique cake each month for $29). And I was able to get 50 email addresses of people who want to notified when the service launches.
What I would suggest you do, is instead of doing a monthly subscription, is make it so when customers sign up they enter all the birthdays or events that they want cakes delivered for, set flavour preferences for each etc. You could then break down the yearly bill and charge it on a monthly basis (makes it more affordable for your customer) or you could bill it say ten days out from when you would post each cake. This model might work better than "receive a cake every month for $x a month" as when people fall on hard times (which they do) they will look at their expenses, and you can guarantee that the cake subscrption, no matter how good they are will be one of the first things to be cut. It would be much harder for someone to cut their subscription to you, if the reasoning behind it was for special events and not just a random cake every month. That's just my suggestion, you obviously know this space much better than I do.
I am not based in the US, so i don't know what your laws and regulations are. However I would assume that the cakes would need to be made in a registered commercial kitchen. I wouldn't imagine you could get away with making them in your home kitchen. And you would likely have to undergo hygiene / health and safety compliance. (This is the case in NZ, however I would imagine it could be similar for you)
Packaging is going to be your biggest area for concern. There would be nothing worse that the special cake arriving in a ruined mess. This would be down to experimentation on your part. Talk to different transport companies and see if they can assist, their might be ones that specialise in "fragile" items.
And with insurance, you will probably find that is included with the transport companies
All the best