I currently live in Madison and am a Real Estate Agent with a Property Management firm here in Madison.

It was close to home and I know the area well.

The long term goal is to put less than $10,000 into fixing up the property and I eventually want to obtain a crash pad.

There are many who are just getting started that think, "well this is easy" and homes always appreciate 10% per year etc. and I will be a millionaire in five years. 

Once they hire property management, they are completely hands off.

Beyond that there are hard money lenders who charge higher rates to take on more risk... but they again start by looking at you, your skill set, and your previous experience in both managing your credit, as well as your real estate investment history.  

., overseeing contractors/property managers, etc.), and 4) contributing the money is worth 25-30%.

My first thought was to review my buyer’s rep agreement and I have requested a copy from both parties.

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?

The equity isn't there in the long run, and I think there is less appeal in these over the last few years.