I fear it might not of happened had I found real estate investing first.

To which I would have no problem with, and no fear.

A couple of my biggest fears as a beginner are 1) Being taken advantage of, 2) Not knowing how to landlord, 3) The tenant/landlord rights in Madison WI – I’ve heard the law favors the tenant heavily (I may have wrong information, I welcome your comments).

The landlords fear that it will lead to warping and replacement will need to be just as frequent.  

Since I speak Spanish and had been to CR several times there wasn't any real fear or concern with that.Note: an issue that will keep many US investors in a post 08' world out of international deals will be the difficulty in securing financing.

Ok, here is one of my fears as a newbie…unable to acquire funding therefore asking for support.

My fear with the money in the property is the fact that Hagerstown prices have dropped significantly in the last 10 years according to bestplaces.net, however our strategy is long term by and hold for cash flow so this may not matter, especially for a commercial property. 

I fear that SFH would be insufficient and lean towards multi unit.

I think the fear of land lording is a fear of making the wrong decisions.

Shoddy work is prevalent.