I am particularly interested in understanding various investment strategies, networking with experienced investors, and finding my first rental property.I believe that learning from others' experiences is invaluable, and I am here to absorb as much knowledge as I can.

But for an OOS investor one consideration is access to support, first of all PM & contractors, and you have more choices in the much larger Milwaukee metro area than in a smaller submarket.

You’ve made a great choice diving into real estate investing—it can truly be life-changing.

The discrepancy between property values listed in their offering statements and actual values (relying specifically on Philadelphia real estate inventory, which is where I am located and have knowledge of property values)Have any active investors cared to look into this? 

Let me explain....Once I learned what others in the group were being fairly compensated (also from Hunter), I quickly realized that I had left 7 figures on the table last year due to my lack of knowledge in this area.

Perhaps they invited Jerryll based on his extensive SEO knowledge and did not look into his questionable marketing methods and extremely high course pricing at $5800 and $19,800. 

Age: I think it will but you can minimize it by being knowledgeable, professional, confident, and fair.  

To my knowledge, the problem with investing in Costa Rica is that there is no financing available. 

Fine - use what ever suits you.Mortgage acceleration is a choice, not a requirement.

When January comes, you will have two disadvantages:- you will have missed on the end-of-year planning opportunities- some of the most highly sought after professionals will be full and not taking clients anymoreAnd the longer you wait, the fewer choices you will have.