Are you using a specific property management software to handle this automatically, or do you have a different system in place to ensure accurate tax reporting?

How long it takes to be financially ready is different for everyone.

What's the difference between co living and shared housing?

I see it as no different from borrowing from a bank.

You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.).

All land courses are the same in essence;What is your end goal is the only thing that is different?

Having separate accounts for different properties isn't super scalable. 

Your not correct under many different circumstances.First property tax is 1.1% (fairly safe) with 2% annual increase (prop 13).Next expenses include a lot more than property tax and interest. 

What are the biggest challenges people have faced with this. Also how do I make sure to get good tenants?

Lenders can have different loan options based on the property type and the amount of rehab (if any) required for the project.