Diversifying to Short Term Rentals - Pros/Cons/Questions

[Nick Ferguson]

I've been a buy-and-hold investor for a while.  I have a small portfolio and self-manage and intend to grow steadily over the next 20 years and then retire.  

I've kicked around the idea of diversifying into short-term rentals (not switching, just adding one or a small handful of properties over time to supplement my regular portfolio). 

I'm in NE Ohio and while I don't plan to completely "self-manage" (ie, do maintenance/cleaning/etc. myself) I do want these properties to be close enough that I can A) check them out personally when needed and potentially tinker/add improvements on occasion myself AND B) if they are vacant for a weekend, go and enjoy some R&R on short notice. 

First and Foremost, how are most of you guys managing these places when you aren't local?  Are you turning over to a full-service management company that handles listings/tenant calls/maintenance/cleaning/etc. OR are you handling booking/listing and managing separate cleaning and handyman/maintenance crews yourselves OR some hybrid/other way?  

I'm specifically looking at Ohiopyle/Laurel Highlands area of PA , Southern WV area (think near New and Gauley Rivers), or rural areas between Pittsburgh and Morgantown. Also, would consider less "destination" type areas like Salt Fork or Portage Lakes areas in Ohio if the price was right and the investment made sense. I've also considered doing a "test run" with an SFR in the Cleveland area and if that does not work, simply converting the unit to long-term and adding it to my existing portfolio. Does anyone have experience with STR's in any of these areas and care to offer any advice?

Finally, how should I think about financing/equity/cashflow factors specific to SFR's? Will I have trouble getting financing on an STR? How do banks look at STR income and debt in regards to DTI and purchasing other properties (whether short or long term)?

Feel free to add any advice but mostly I'm just looking for things an experienced investor should think about when considering pros and cons of diversifying into short-term SFR's.