The outcome has been great so far (minus the past month with COVID - travel has been down, but we have still been able to cover costs with longer term bookings at a discounted rate).

It makes me a bit nervous to think about investing out of state, but if you know the area, you have family near by, and you're likely to travel to that area fairly regularly, it makes sense to me to invest there. 

It's an uncomfortable situation and not a conversation I'm confident of or can even predict how it will go.So . . .

Need the financial backing, knowledge, and team first, however; it’s a multi variable equation where each part is equally valuable, and even interchangeable, and when the sum of them is great enough to feel confident, it is time to invest.

Depends on the individual investor, their current age, etc.Someone's idea of retirement might be living on 30k a year and traveling the world on a shoe string budget.

This is a travel industry crisis not platforms.

I am now leaning towards selling my condo as I am not going to be able to rent it anytime soon (also not confident it will cash flow well due to high HOA and taxes) and I would get much more from selling it than I would on a cash out refi.Like others have mentioned, I would suggest diversifying your capital into as many properties as possible that will cash flow.

Made me feel much more confident in my decision

That speaks highly to your confidence and competence in the work you've been doing.I'll share what I do in scenarios like this. 

I travel often and am worried in case of small violations (appliances left outside, grass not mowed by tenants etc) that I won’t be able to notify management quickly enough to fix the issue.