It is a fun experience, you will make great lifelong friendships, and it sounds like you already know you want REI to be a big part of your future. 

This can save headaches and friendships.

Even if you have a group of friends who want to lease together, always give each tenant their own lease, just in case their friendship does not last the term of the lease.As to pitfalls, Tim Breems makes a good point about checking for HOA restrictions/fines.

I am struggling with the following:How to properly value this property considering the condition it is in...How to value an awkward and somewhat unusable acre...it is shaped like a large splinter.Wanting to maintain friendship with my neighbor and respect her and her property while still trying to get the property at a price that makes it a wise investment...Emotionally, I really want this property because of what I would love to do with it.  

Anytime I have mixed friendship in deals it has softened the line on the business.

My first experience as a landlord was in 1987 while having a full-time job, raising a family, and maintaining friendships.

Friendships are harder to verify than family so you should be okay. 

By doing this, I can provide practical guidance and have others weigh in on the conversation as well.We can solve a couple of items like acquiring new knowledge, and help us form valuable connections and friendships along the way.

Jaago Viitkin gain some friendship through one of the Board Members of the HOA.

I have to watch that my friend is satisfied and not let the money to ruin the friendship.