Hi Makani, I believe that staying positive is great cash flow in itself. 

I personally would stay away from condo-tels as they will be even worse and you'll have less opportunity to cash flow. 

Since this situation was so egregious (IMO), I would either boot them out now, or at least have a serious talk, real serious....If you're going to let them stay I would just get a really deep cleaning done, maybe a couple, and then replace carpet after they're gone.

@Abby Chapman I would stay clear of NewWestern/Net Worth.

We had hoped to rent our house for short-term or mid-term stays.

Most softwares will list (at least) name of guest, stay dates, ADR, and revenue to owner.

@Katie Lyon Because our weather is more temperate over the winter months, we have much more consistency in demand across all times of the year, so typically the market stays fairly consistent through all seasons.

Hey Marc - Offering free Netflix can be a nice bonus for guests and make your property more appealing, especially for longer stays.

I plan to stay overnight for a weekend trip in the next week or so. 

Buy a quality property, stay away from the hood, rehab it as if you would move in, take your time picking a tenant, you'll be find.