If you can't get an answer from your HR department or CFO, bring up the phrase FIDUCIARY LIABILITY to them.Last resort, I would speak to an attorney that specializes in ERISA law.

I was just Skyping my father, with whom I discuss various investment opportunities; he mentioned a venture he has invested in recently.He has invested in a conglomerate who own various resorts around Australia, his buy in bought him a percentage in a particular resort (a beautiful beach side resort).

You may have good intentions in thinking of a sub2 as a last resort, but as @Jay Hinrichs mentioned, there are substantial risk associated with this, for the Seller.  

I would have to get a mortgage but I can almost guarantee all year round renters.Scenario 2 is a small chalet up in the ski resort that will cost 40,000 and predicted 9% annual return.I can buy this outright.Is there a rule of thumb for these types of investments?

Last resort, depending on the foundation type, dig down to the footings on the outside of the foundation and re-waterproof properly.

I've used Tripadvisor a lot in the past but only for looking up reviews on hotels/resorts, restaurants, etc.

Thanks Ken.Matt, I'm not an attorney, but my thought is along the lines of the time share arrangement used in resorts.

I've been tempted to reply to these types of ads before just to see what the deal was but in the back of my mind, I couldn't rationalize why in the world these guys had to resort to CL to find someone to fill those "positions."

I personally like resort areas like San Diego, Maui, Hawaii and Park City, UT.

Michael,I would love to have a beach front condo or home in a resort area.