Something that is ski-in ski-out  or in the Village is always going to rent for more, but is also going to cost you a lot more upfront.

The cash for keys is really a last resort before evicting them from the property.

I paid $147k for a 1-bedroom condo here (ski resort area in winter, close to Yosemite Ntl Park in the summer) and have been averaging a bit more than $3500/month gross in the 9 months that we've been renting it on Airbnb (I think we might even be able to raise that a bit as we move forward, since we were just starting out, figuring out the system, getting reviews, etc.)

As a last resort you might consider Gillette. 

Good point @Nick Colamarino ...would this be a scenario where you offer $3k, $6k, or $10k as a last resort?

While I won't have enough to buy real estate, I have more than enough to engage in private lending.The fees for setting up and maintaining an SDIRA are higher than a "normal" IRA, but I believe that the income the money will generate will make up for it, after the initial year.Withdrawing the money and taking the tax hit would be my last resort, but if you are aware of the penalties and taxes that come with such a transaction and you are ok with the amount of those, it is your money.The key in my mind is to see which option fits with your overall financial picture and your goals in real estate.Good luck and I hope this helps.Ed

And I don't think you need to resort to 'predatory' lending, or deal making practices when 'sizing- up' a potential buyer that isn't likely to 'default,' on their loan.

If you can say "I bought my house with a discount and it has appreciated" EVERY time you need/want to move to continue with that strategy, then - the sky's the limit!

The Bank of Canada never had to resort to the full-on money printing that harder-hit countries undertook.

A 5% repair expectation is also typical, and some banks require CapEx reserves (depends on the bank and if you are classified as 'resort')  So Your $300 is more like $100.