I am concerned that it appears you are considering renting to someone you have known many years.

Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/meetSet up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alertsRead Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingIf you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

We are pre-boom and it is more valuable to have the property than be too concerned with Cash Flow.

My only concern is getting approved "multiple mortgages".

I have questions about the process and what you got out of it and if it is truly worth the money as a beginner to real estate investing

Many have posted a few great tips already, that's the cool thing about this forum ;-)That said, I highly recommend using the awesome tools provided here on BP to learn the basics of analysis and underwriting.A few tips to get started and your continued learning:Find and connect with other BP members that are in your area.Set up keyword alerts to be notified of the topics that interest you.Read Beginner’s Guide.Check out BP Podcasts.Find upcoming real estate events and meetups near you.If you'd like to tag someone in the conversation, type @ followed by their name and then select the name of that person that appears below the comments box.

Other concern is we are continuing working on adding more properties to the portfolio so within 5 years we could have 5-10 more properties.

My concern with including closing costs in the Cap Rate is that you're often paying points which ties into Levered CF.

Specific topics I need help with are: should I look into majoring in business as related to real estate (perhaps getting an MBA) or is this a waste of time, when should I try to buy my first property (as in how much money should I be looking to spend), what type of property would be best (apartment building for rent, SFH, wholesale, etc), what banks would be best to get a loan from should I need one, business and real estate books/ebooks I should read, and the pitfalls/rookie mistakes beginners make. 

Are the bigger dogs not concerned with newbies and their “no money what to do posts”?