What questions should I be able to answer before starting out?

[David McClain]

As the title asks, what questions should I be able to answer on my own before starting out.

I'm new to the mindset of RE investing (although I've owned my home for about 7 years now) and have been trying to learn as much as I can. 

I get that there might not be any way to really 'know' when I'm ready, but the more I read/listen/learn, there does seem to be a pattern of fairly common problems people run across, or steps that they have to take.

My current goal is to try to buy my first rental property before my next birthday in May. (Whether or not I reach the goal isn't as important as having something to aim towards). 

I understand that sometimes you just have to take the leap, but I don't want to jump in too quickly. I don't want to be in a position where, if I would have asked, people could have said "Yea, you're obviously not quite ready, you should have done A,B,C, or learned X,Y,Z".

[Josiah Kay]

Personally, I believe the most important question to be able to answer is "Why are you choosing real estate investing?" The answer to this question serves as a foundation to everything else.

Once that question is answered, you will be able to answer the next question of "What avenue of real estate investing is most conducive to my 'Why'?" This answer should continue to drive your choices as you invest. Personally, my "Why" is so that I no longer have to trade time for money. I am choosing real estate because it offers me an opportunity to spend my time on things that I want to spend them on. For this reason, I chose a real estate investing strategy that will require less of a time commitment to manage and is suitable to allowing me to "retire" early. Knowing the answer to this question will help keep your focus and your actions aligned with your 'Why'. 

Since your strategy is rental property investing, I would highly recommend reading "The Book on Managing Rental Properties" by Brandon Turner. That book is a treasure trove of great information. I would also recommend "HOLD" by Gary Keller. This goes more into the analysis of deals and is a good starter book. Lastly, I would recommend "E-Myth Revisited" by Michael Gerber. This book will help keep you working on your business instead of in your business. Combined, I think these three books combined are a great Starter Kit to rental property investing. They should position you with the necessary knowledge to jump-in.