Hey Topher - welcome to the most fun ever. I'm similar to you and Jeff - corporate exec professional guy, got into wheel to wheel racing 11 years ago. You are approaching the whole game very well. Get solid and reliable tow vehicle and trailer. Get a well built ITS car - that's where I started. Its a fast class and allows a lot of growth. Big fields. My suggestion - Buy a 3 series BMW - you can't go wrong and it'll have all kinds of other potential for other classes.

Or go for the Porsche - I think they're the best but you will pay a premium :-)

Keep us posted - this forum is tremendously helpful and we've got some trolls and other oddballs to keep the posts interesting.