When the tenant admits to struggling to pay rent, it's inevitable that you will have to deliver a notice to pay or vacate.

I have to admit that as an Ohio Realtor.

Due to horrible, and I mean horrible property managers in the area (the one known as being the best admitted to me she recently had an employee steal over a million from landlords and she didn't think it was her fault), I decided to hire a family member full time to start managing properties for me. 

They don't care about your property, won't suggest the improvements, and just live of you.I self manage AirBnb in Seattle and hired a remote PM in another property and should admit that if the PM is not local I could do the work and take care of the property much better than a hired PM.

My $10k example was admittedly unrealistic.However, by way of further background, @Dustin Heiner wrote an excellent article on this topic on his website masterpassiveincome.com titled "What to Do When A Buyer Backs Out From An Assignment Of Contract".In it he suggests a scenario where the assignee decides not to proceed, perhaps after discovering a big ticket repair item that would cost significantly more than the portion of the assignment fee held in escrow. 

When i asked her about the maintenance fees. she openly admitted in writing that vacasas' primary obligation is to the satisfaction of the renter and that they have no obligation to the home owner beyond changing lightbulbs and cleaning the linens. 

The owners may agree to carry part of the financing, but you won't need them to stick around to transition operations.After acquiring the properties and assets you wish, you would either run your own business, or part-out and resell some of the assets.From your post, it does not sound like parting out the properties is a viable path and where you admit to having no experience with vacation rentals or the resort business, you might want to explore purchasing the business with the current owners hanging around for a bit to help you get your feet wet.Regardless of approach, it needs to have legs to be worth pursuing.

Starting with $50,000 and house hacking, to be honest, that sounds overly optimistic, which is admittedly not something I like saying.

I have tried a couple times to get ahold of someone to do this, but I haven't been able to get much traction--I will admit, I quickly get distracted with other things and forget to follow up.Is the right way to go about this just pure persistence, or have others had success buying from large corporations like railroads?

They had planned on moving back home but he ended up getting admitted into the hospital due to his lung issues.