My thought behind it was to simply get rid of debt and take on less risk  sure, if you are deleveraging across the board but if you are going to turn around and buy a new property with leverage that does not make sense. 

I get get really good prices for home games, graduation, ceremonies, moving kids in and out etc.I get all these bookings from VRBO.

Starting with your wife and possibly your kids depending on age (for example, they can help clean between tenants, this starts  their education [Check with your accountant because you may be able to pay your kids and take a deduction].- - While you will do the lion share, can you take advantage of your wife's talents and availability?

For other deals Im happy to be a sounding board.  

People who are younger and don’t have kids - are looking for the up and coming trendy spots.

I am single with no kids.

BTW: did you check local ordinances about boarding room rentals (which this would be)?

My parents have an apartment in Vancouver that they are debating whether to sell it or pass it onto their kids.

I'm in Orlando and active in residential real estate as a Realtor® and also serve on the board of CFRI, the local chapter of the National REIA.

Family becomes brutal when its time to split up land or decide what to do, plus with the heirs laws you or your siblings kids have rights to the property.