I started my company as an LLC. Since it began in Pennsylvania, I registered as a PA LLC. Welp, I applied to Y Combinator and they accepted me, but it turns out they won't invest in LLC companies. I figure, no biggie, I'll just convert to a DE C Corp as I'd been planning to do eventually anyway. It turns out this isn't so simple for dissolving a PA LLC, and it is a several month process. I almost wasn't accepted into Y Combinator as a result because they aren't going to wait several months before making their investment, and was only able to attend because a very experienced lawyer found a loophole to convert my company into a PA C Corp.

I am still suffering headaches from this, even after my company shut down, because of all sorts of bizarre issues of being a PA C Corp. And since nobody knows anything about PA C Corporations, I can't use standard documents and legal advice is particularly expensive (and usually not the best).

Corporate law isn't always so cut and dry.