My 8 plex needed a roof, heating system, a monitored fire alarm system, and remodeling of many of the units as they turned over, not to mention many 'smaller' plumbing, electrical and cosmetic repairs.I bought it anyway. 

Monitor your area and find a fare value. 

There are usually some good, local investors that monitor those forums.

I am monitoring the Louisville, Kentucky market and the proposed regulations.I am new to the STR space.

I than went back to doc and told him, "one of us is going to medicate and manage my pain". 1) He can give me back my meds and monitor them, Or 2) Im going to continue drinking uncontrollably, and probably end up dead.  

One was a bad property in a bad neighborhood bought at a wrong time (right before 2008 crash).Another one was more recent and happened because one of the GPs turned out to be a crook.

You will be able to monitor your score more closly if you subscribe to the service.

If your system is automated and you have security in place that can be monitored remotely, you really only need boots on the ground for a few hours per week and that should be pretty affordable.There's a lot to know and I don't have time to write a book about it.

I regularly monitor many of the Broward County markets so if there is ever any info you need on a market or you are actually interested in starting to analyze potential deals, I'd be more than happy to connect you with some properties that meet your investment criteria.

I would also LP on a deal or two and get on a bunch of GPs mailing lists to learn from other people doing it.Syndications and being a GP is a lot more, work, time and effort then many make it sound.