I think buying attractive, move in ready properties and possibly making small updates to make them look more stylish is the way to go.

Income would cover rent for a short time.

Many times, when i replace a water heater and take a look into some of the short pipes that connect, they are approx 80 percent closed. 

Quote from @Jeff Roth: Hi Lina from Texas-Congratulations on your interest in investing in mid-term rentals and you are wondering how and where to get started.I get this question frequently from investors.Sometimes and investor is looking to keep their property cashflow positive as insurance and taxes have squeezed cashflow by turning units into mid-term or short-term rentals.First off, ideally, the property will cashflow as a long-term rental should something disrupt the mid-term rental model.You will also want to have the property be near where there would be a demand for mid-term rentals (hospitals, universities, research centers).Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.There are property managers that will manage mid-term rentals for you and I always advise my clients to use property managers to keep their investment as passive as possible and for compliance issues related to Fair Housing Laws and local regulations.To Your Success! 

So long story short I am still hunting down the contract. 

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These were investments, the value of the assest are there, its the liquid that ran short and had to resort to credit cards to fix up the propertyYou spent $50k from savings, borrowed $50k from a 401k, and are paying it back over five years at around 7.5% interest, then borrowed another $40k from credit cards and are paying that back at around 8% interest, maybe more.

I was just on their website looking at the permit process:CityofSac-STR PermitLooks like 90 days max until you get a conditional use permit but still reading as it seems a little unclear:A short-term vacation rental may operate from a location that is not the operator's primary residence for a total of 90 days in a calendar year.

If he has a $5MM loan in place, what was that used for / is it coming due/ was it short term/ etc.?

If you’re short on funds maybe seller financing or subject to deals, where you take over a seller’s mortgage or negotiate direct financing with them.