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

It depends on your personal situation.

This will depend on down payment and the property's layout.

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.  

If the answer is no, it would depend on your current income.For a purchase price near 550k, I would assume that it would be cheaper monthly to own compared to paying 5k.

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.

Take Indiana for example you can still buy a Multifamily 2-4 units from $90K up to $350K all depending on turn key or need renovations.You also have states like Tennessee, Alabama, Florida, Ohio and others that offer great LTR and STR opportunities.