i've managed both OOS and in-person and both can be a pain but OOS is just harder for most new investors, period.

Some of it is just a royal pain in the ***.

That might mean only pain $10,000 rather than $25,000 that a contractor might quote you.

It’s very hard for me to see almost anyone I can think of giving up thier mortgage that’s cheaper than renting in most cases because of acute financial distress, certainly the region could feel pain as people cut back in other ways like eating out, travel etc. but the number of people who will be forced to sell I suspect is in the low single digits..I don't live there, I don't buy there.

@Andrew KatzIn this situation, you can either (a) continue dealing with the pain of having your tenants that pay late and violate your lease terms or (b) deal with the pain of turnover but the prospect of getting better tenants. 

There is another STR owner in this community I've talked to, and he's been doing it for 1-2 years and he said it's still been a real pain to deal with. 

I feel your pain when it comes to the high cash flow, but low appreciation and potentially high maintenance properties.

Learn about the seller, their goals, their pain points, etc... then present solutions to their problems. 

@Joseph Sakic the "pain" is directly related to:1) How much your current PMC cooperates2) What paperwork you already have or can get to send to the new PMC

That would be the biggest pain point when moving.