If you're using the VA loan system to property-hop after each minimum time requirement, you should already be aware of how hard it is to "house hack" for FREE, given the difficulty of finding genuine bargains that also meet the VA's liveable condition requirement.

@Federico Gutierrez :-) I guess the leaseholders are not biggerpockets members :-)@Frank Sanchez How difficult is it to evict someone in Chicago in the winter?

If you screen well, you should have no difficulty finding good tenants. 

As far as my knowledge in real estate, I am just a beginner and have a lot to learn, apart from buying my own home, reading books and blogs, taking my realtors license and working for an investor I am just getting started, but coming from a career in web development and internet marketing I am well versed in the technology side of things and am looking forward to getting stuck in to help and learn.ThanksGuy

How difficult is it to register with the SEC if necessary?

You're going to have difficulty finding lenders willing to lend on that amount.

What are some of the difficulties or successes you guys have faced with this?

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.

@Jeffrey Holst I think many ICOs on blockchain technologies will have great technical underpinnings, be useful, stand the test of time, etc. 

To renew the lease, they wanted some repairs and improvements which I agreed to do.We did run into some difficulty with installing new kitchen cabinets and the tenant could not use the kitchen from Friday to the next Tuesday morning.