Some told me to dive right in and others told me I needed to take a specific path meaning I had to take certain steps to get to the top.

this question is being asked here ALL the time for every area in the country. and it doesn't get any answers (99.99% of the time).that's because i (assuming it's true for everyone else) would never share my contacts with a competitor in fear of losing that contractor. kind of like setting up a blind date for your spouse..just being honest, that's all.

But for myself, I prefer a more smoother path.  

And what if you decide down the line you want/have to work in another country.

You can use an FHA to get into a duplex for 3 1/2 percent down plus closing costs if you are going to owner occupy ( reside) in it for at least a year.If you want to flip without a lot of money - well that going to be a tougher gig - you may want to see if you can partner up with someone who does have the money or maybe you can match funds - either way the point is a partner can open up doors to paths you may not have thought were available.

CT has some of the highest licensing fees in the country. 

@Jay Hinrichs Well done working across the country.  

We are just starting out in the real estate business and currently are unsure of exactly what path we want to take.

However, unincorporated areas like wine country do allow them.

Good luck on your first deal, In my opinion you're on a damn good path.