The #1 reason that Landlords fail, according to the American Apartment Owners' Association, is the landlord's failure to manage to the lease.  

Instead of a co-host can you just get a property manager that specializes in it?

I also have not had (Knock on wood) too much time spent on managing the properties and keeping them rented to long term tenants.

Cash flow depends on the down payment, but using a HELOC could keep your cash reserves intact while you get started.Make sure to build a reliable team (property managers, agents, etc.) to help you manage the property while working full-time. 

If you are managing this yourself, you are off to a great start.

Use AirDNA to get a better feel for what may be projected and then dive into Airbnb and compare to your competitors. 

And the cracks mostly follow the drywall seams from what I can see, which is typical....And as @Patricia Steiner said, it doesn't look like a pro installation....You could ask the Contr to use a flexible compound if this happens again, or maybe even now...https://www.dap.com/products-projects/product-categories/pat...Like everyone else said, I'd have it repaired - by a licensed Drywall Contr. - and then just check in on it.

However, I’d like to have a space of my own before living with others again (I plan to house hack again with my next property).I’m seeking advice on how to move forward, as I need to consider things like utilities, taxes, landlord/umbrella insurance, and managing the property, especially with someone renting my garage.Specifically, I’m curious about renting out individual rooms and living on my own for a little while.

Heck it's so good I could manage a loss for a few months but I really think the cash on cash return will be 10% + first year and 20%+ 2nd year. 

Start by being actively involved with your PROPERTY MANAGEMENT duties.