You're getting wrapped up in how difficult your tenant is being instead of how difficult the job is to accomplish with the tenant's behavior being what it is.

What"s the best way to accomplish all three? 

Maybe Biden will forgive your student loans and you'll have the ultimate real estate house hack triple back flip accomplished too. 

To be frank, I think even getting a property in contract is quite an accomplishment itself!

Allowing people to use their rent money to throw parties and buy big-screen TVs does not make anyone better off or safer, it in fact accomplishes the opposite of what is intended.  

This should be able to be accomplished without a taxable event.

It's easier to accomplish, enforce, monitor and regulate.  

It will be a relatively hard goal to accomplish to find one within 15-20 minutes.I can send you a list of what's currently available within a radius of that zip code if you'd like to take a look for yourself.

It depends on what you are actually trying to structure and what you are trying to optimize/accomplish.

.- Is this a transparent standardized process, or could only be accomplished by well-connected folks..:)Thank you in advance.