I'm all in but I must admit the whole game does feel a little intimidating, anytime I think I like a property and I think of calling the realtor, I start having self-doubt (that maybe I'm missing something and I'll come off completely stupid).I would like to ask the seasoned investors, how was your experience with your first deal?

I strongly recommend doing something with getting Books in order for Tax season, this gives people 3 months to get an idea of what they can do to make it easier on them and possibly cheaper. 

While basis adjustment may seem rather self-evident, appropriately navigating the particular tax nuances often requires a seasoned practitioner.

I am a seasoned marketer for Window Installers.

Figure out what season investors in your market are doing and how they got started (investor meetups, seminars, etc.).

When you do it yourself it will require more time from you and also in slow seasons you might not make much money.

@William Johnny If you want to get into real estate, you mostlikely need to be earning $100k plus, yoi should get your real estate license and start aprenticing under a seasoned investor.

For now you've gotten some great advice from some seasoned tax professionals. 

In my market and markets around me you can get a high quality rental for 150-300k.Rentals aren't feasible for everyone especially if you're in a market that's super expensive and not a seasoned real estate investor this is what leads people to invest out of state passively. 

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.