There's something to be said about experience, and you may lose a deal or to working with a rookie that could have been save by an experienced agent.To Your Success...

You're not in this business to lose money.  

I'm going to say that it depends what your goals are in seeking education.Cruising these forums, you'll see stories where people lost money because of what didn't know or didn't know to watch out for.At the same time, you'll find a pervasive and powerful bias against paid education.You'll want to decide for yourself which is the greatest expense: losing money on a deal (may or may not be deductible) or paying for education to help prevent losing money on your deals (deductible as a professional development expense).

If you are working one property at a time and buying right and not only spending 6 months you probably aren't going to get stuck - most likely the worst thing that could happen would be that you would lose the anticipated equity you are building.

The investment amount isn't as high as E5, but must be "substantial" and all at risk, in other words, you must demonstrate that you run the risk of losing it all.  

@Mike Alder  good luck I grew up in the business.. must watch movie for any land man is Glenn Garry Glen ross... you will see how all these lots you want to buy were created in the first place.land game dates back to just after the turn of the century  ( not 2000) when promoters went through the US creating mega subdivisions prior to any state or federal land development rules.. so you have all these old tracks and the parcels have been traded for 100 plus years.. lost at tax sale bought by someone like you or my dad.. resold on terms  those folks default or lose to tax's and the cycle repeats.Florida created massive subdivisions to attract residence's since no one wanted to live in swamps and such.. think Le High and Coral Gables..  

It was my first real estate transaction, everyone told me it was a bad idea, one friend begged me to lose my deposit and renege (she is now investing with me :) The only supporter of this purchase was my painter brother, who showed me how to spray paint, so I put on a hazmat suit and primed and painted the walls, ceilings, floors and inside of cabinets. 

They would be losing 30k on that. and you can't lower your mortgage by getting rid of the ARM.

That urgent care can lose money (many do) and hence not be able to make lease obligations.  

If you rent both sides and lose one tenant, not out rental income 100%.