We started pricing ours a lot higher for the long stretch, and there are still many people who book those nights. 

Since you plan on being here long-term, the best way to beat the cycle is to buy a home with a long-term strategy, where the monthly cost is affordable (never stretch yourself to be "house poor").

I know it could be a stretch but may be worth it over the longer term.

It’s getting really tough to find deeply discounted deals because sellers know how strong the market it and buyers know that they have to stretch to buy deals. 

I have to agree with you on the money pit analogy being a bit of a stretch. 

If an emergency were to arise it could be available again; and CC debt is the worst kind to be carrying or stretching out.

This property is so deep into negative cash flow that it is not a investment by any stretch of the imagination.

My first thought was even if I break even, Ive got a condo building equity... it would however stretch me a little on debt to income.

Overall we ended up making just about 8% on our money not a slam dunk by any stretch of the imagination but at least we didn't lose money and we learned a ton in the process. 1.

Right now I self-manage 6 of my units and use property management for the others just because I’m stretched too thin w full time job and a family and i also do a flip or 2 per year.