This is a model of retirement I could get behind.In order for this model of retirement to work, you have to imagine that you could find a way to generate income without you having to do anything (i.e., passive income).This additional income would cover your living expenses, or perhaps even more, making it possible for you to quit your job and start a new adventure, or continue working your job, but with the mindset that you get to do it, rather than have to do it.Retirement 2.0 is not a stage of life that comes at the end, a last hurrah.

Plus, imagine being your own tenant - would you even rent there?

I couldn't really imagine my life with out a job.

I don't have the cost of the paint alone but I would imagine it's somewhere around 2.5K.

I can't imagine any renter leaves it clean enough to move in a renter right behind without decent cleaning it unless you had a diligent renter that paid for a cleaning.You could add a clause in your lease stating a charge for cleaning upon move out if you insist that the renter cover the expense.

I can imagine the competition among STRs in the coming years could be brutal with a flooded market.

I imagine seeing pet Elephants now. 

Ask every single awful question you can imagine.

@Ashley Wolfe Totally agree with what @Lucas Carl just said.We managed our guests and I remember it was a lot of moving parts so I personally couldn't imagine managing other peoples' guests... 

Happened too many times for first 3-4 years.There is no risk of loosing the "deposit" either and it's just a bit of skin in the game even tho the skin is always yours to keep heheCovered all angles mate and made this as fool proof as possible but still enough to make folks "jump" through hoops to see who is legit and who isn't.As Chris mentioned, 90% of investors we don't end up working with and even when many commit to the deposit, I refund many times as I don't feel a good fit.Even with such stringent criteria, we still get mud thrown on us here on BP as some folks slip through the cracks.I could only imagine if we took on everyone and just focused on pushing sales.I can sell a TV to a blind man and ice to an eskimo.