My parents will be 80 in 5 years so I know we are at a crossroads in having a talk and seeing what they want and how we can accommodate that without jeopardizing their financial security.

It feels like we are running out of room.

It is by far the nicest home in the subdivision and we are receiving an incredible amount of interest via Craigslist for the home at $1,500/month.

Then once we are at 60 days closing escrow and officially recording.

I believe it is required that we a) reveal our status as licensed agents and b) identify the brokerage we are currently working with.  

You don't want to be that guy :) I'd hate wearing a suit and having to shave and look pretty every day :) Just keep it up and you can wear whatever you want and drive whatever you want in a few years :)

Gary West, just another item to consider in your one-at-a-time approach, but markets and interest rates fluctuate, and while Feb 2014 probably won't be that different, waiting several years for each one may hurt your ultimate goal as right now we are still in a record low interest rate environment along with low home prices, but in 5 years, you may be looking at 8% rates or prices too high to justify buying to rent them out.

LOL) We are builders, so our viewpoint is somewhat different than those strictly investing to hold, etc.

Besides the natural damages, vacation rentals can incur higher wear and tear damage from different people moving in and out all the time.

We are mainly concerned about not getting the list that we want.