Buying your own home is NOT.I guess I don't see the distinction between what your are looking at to what I am. 

They tend to be older, have more money and leave the places cleaner.The difference in the 2 platforms is also distinct.

Phoenix is way too expensive (I live at 37th st and IS) and with a  market crash (stock and probably everything else) in 6-8 months a distinct possibility no way would I buy in bubble 2.0 Phoenix land! 

The OP distinctly separated AIR and VRBO.

DONT USE SCENTED BLEACH  .

Therefore, I would recommend separate LLCs for each distinct partnership or business.

As Stetson mentions, there does seem to be a distinct high and low season.

The policies are also distinct for long-term versus short-term rental properties.It is worth checking with your original insurer to see what kind of policy would be needed overall (both units).

Your name is distinctive enough that a number of us just won't pay attention to any questions you may have or any responses you might give. 

Andrew a quick clarification here....there are actually two related and distinct categories of units listed within City of SD; Companion units and Junior units....While the Junior units do require owner occupancy, the Companion units regs do not list that as being required.