I think if I can achieve that I will rapidly learn, then be able to evaluate what steps might be best for the next stages.

Your first step is definitely learning about the markets you are interested in and figuring our what your desired end state / goal is that you are hoping to achieve through real estate.

As someone that over analyzes things as well, I’d suggest you step back and think about what your goals are in order to help determine what path to take.I like JD’s suggestion about reinvesting in your business.

I plan to never pay tax on the appreciation with the current tax rules (1031, die with step up basis, etc).Best wishesYou are way off topic.

Quote from @Shayan Sameer: Quote from @Zachary Deal: As several folks have mentioned leveraging equity in current property you owned is a great tool but still comes with the some of risks as you had before using hard money debt as there is never a guarantee your new project will be a success (there will always be risks with real estate investing).Leveraging your investment property would probably be the first step I would take. 

@Caleb Rehg  I would advise your first step is to search this site for college student rentals and student rentals and read all you can. 

Do you have a step by step list when looking at the potential house?

Even a small first step will teach you so much, and with your analytical mindset, I have no doubt you’ll make smart decisions along the way.

. - 2 story house with very small rooms and and 2 steps down, imminently as you enter the front door.- Gated community and in a reasonable HOA. - The home is 2 payments behind and already got a letter from the lender about future foreclose.

Our experience is that many lenders/servicer customer representatives may not know the protections that exist for those that want to put asset protection steps in place.