The rules vary locally. 

During the draw request process, it can take several business days (sometimes a week) for the draw to hit your bank account depending on how much they push back.

Not to sound like a jerk, but it may depend on what you define as "a deal."

It depends on your personal situation.

Not too say that you should do the same thing, but it depends on your goals.

I might also be looking for an end buyer, private money, or partner for this deal depending how the numbers shake out. 

It really does depend, you don't need the LLC setup to do the things you want to do and you'll still get the tax deductions.  

Quote from @Glen Wiley: I suspect that once I retire from my W2 I will probably set up a direct booking channel since I'll have more time but for now I am accepting the risks of depending on the OTAs in exchange for the benefits. 

BUT I won't be dependent on them.

It would also depend on how much the rent will increase after the lease.