However, I’m wondering if anyone here has had success investing OOS in locations hundreds or even thousands of miles away and still managed to maintain solid cash flow.Have you been able to overcome the challenges of investing in a distant market, and what strategies or systems have worked for you?

Cities like Cleveland are so street specific, getting a pm based in dallas, staffed by VAs will ruin your investment. 

Guests staying more than 30 days are likely going to cook at least some of their meals, and nothing ruins a stay faster than opening up the cupboard to discover worn, dingy, and damaged cookware.Best practice: Buy a new, inexpensive yet COMPLETE set of cookware, containing at least a frying pan, a covered skillet and two sauce pans.

Too many people your age is lured by wholesaling, but 99 percent on wholesaler fail and can ruin seller's hopes along the way.

I wouldnt advise on ruining someones career, but I'd solve the problem as peacefully as possiblySilence isn’t protection — it’s liability.

It could Potentially save you thousands or 10s of thousands 

It ruins the value of your property.  

@Kelly Schroeder too many investors focus solely on the PRICE of management, which often means they sacrifice QUALITY of  management.Then they find out the hard way that bad management can ruin the best investment:(

And hurricane Helene only added insult to injury, meaning many people still think we're partially closed or that what was once wonderful has now been ruined (both of which aren't the case).

Even though I had insurance and had even added on a couple optional items, it was death by a thousand cuts on the repairs.