What's the best way to do this, and how much would you expect to pay for this extra layer of management/oversight? 

Maintaining an affordable housing supply is a vital component of the American economy.

( wear layer, thickness, padding, price)What surprised you the most with this product?

Without seeing it it is really impossible to say but if it has 2 layers (given your post this would seem likely) and it has multiple leaks to the point it is causing interior damage and you (or someone) has done repairs already sounds like it is time to bite the bullet.  

See, as a patient quality of life is vital but being imprisoned to appts and treatments makes it hard to travel anywhere much unless to drs so I’m thinking if I theme each STR differently from decor down to even snacks etc I may stay booked a lot but mainly it’s my way of making a difference.

If you're new and doing one house at a time without employees, an office or other overhead, pretty much all costs are going to be COGS (costs directly related to your properties and renovations).As you start to scale, your expenses will increase, as you add layers of management and other overhead costs. 

Use LUAN board, sometimes two layers of it.

Thanks @Russell Brazil This is getting more complicated with layer unpealing.   

@Eric Bilderback -- China's new economy is a fusion of the communist power structure plus wild west robber barons layered on top of each other, with a huge dose of mafia-style organized crime behind it, except the criminals are all in or connected to the government. 

Remember, it's vital to have good relationships with agents, mortgage brokers, insurance agents, ect.