Do you flip or hold?

He sounded very guru-y, claimed that flipping houses is "easy", and used the entire presentation as a pitch for a "class" he is holding two Saturdays from now.

@Matthew GaineyNot an expert, but perhaps I can help:Say you want to buy a house to buy and hold.

However, those holding a professional license should call it as it is; a "Sale Associate" or a Real Estate Licensee.

Based on the numbers it is not worth the issues you will face to hold it.

If you have a deal which will give you cash flow with enough margin that you can hold it through a downturn, and you have the courage to hold it, then perhaps now is the time to invest.  

Doing the math I figured with a 4 bd home I could rent out each room for about $500, $600 for the master bd, is $2100 gross rent minus the holding costs of utilities, mortgage, cap ex, etc, (1700) = $400 net cash flow (calculating if I didn't live in it, if I did I would be paying out of pocket $100/month to live with 3 other people).  

.- Interested in rent and hold SFH, MFH and >4 multiplex properties.- Happy married with 2 kids!

@Jason JonesI have to step in here and state that a Rollover as Business Startup (ROBS) plan does not align with your situation as you have described it at all.Those plans are for actively running a business, not holding passive income properties.This is a complex and expensive solution, and a great tool for certain situations and significant amounts of capital.  

If I were you I would hold the 2 current vacation properties in separate LLCs and cash out refi them.