However, in this low interest rate, slow growth economy environment, everyone else has been thinking the same thing for several years now.

Brandon has BP, Ben Leybovich has CFFU, and others just continue doing things within real estate (PM, flipper, broker, realtor, developer, etc..) to reduce the turbulence.The concept of retiring quickly using RE has been published in blog posts and mentioned in several podcasts but it is oversimplified for mass media production.

Even though I would love his input, that isn't where he is right now, his healthy dose of skepticism however does slow me down and makes me make sure that I am going in a good direction.I ordered books, listen to podcasts, post and read the forums.

I like the strategy of the long term tenant during the slow season...if that is the best you can get for the area and time of year.If you are able to generate the $130 per night during the peak season - that would bring in $12,675 at a 65% occupancy rate ($130x98) (there are approximately 150 high season nights) but you are only bringing in just over $8600.So it sounds to me like you need to focus on your short term rental occupancy rate and maybe make a rate adjustment.  

We do our best to mitigate for the tenant, as required, but a late summer lease that isn't occupied can put the vacancy in to the slow months, with a longer vacancy.  

My problem is I think the market will slow way down and cashflow on leveraged properties is becoming a thing of the past. 

I think it would be great to eventually turn this into a full-time gig, but slow and steady wins the race!

@Jeff BridgesI'm always a little bit hesitant to recommend placing an umbrella over the top of another carriers products.

. :)You can pay $6,997 to ask him at his "Power Players" seminar in Maui this November. http://www.thecorco.com/products/power-players-whistler-2016Both of my friends go to this event every year and swear by it.

This product has been around for awhile already.