The tenant you're looking for who can afford that aren't looking to move in the winter during the holidays, so it could be timing, but what will you do to convince them to move now? 

I am currently in the San Diego area and looking to begin investing in rental properties in the near future but my wife and I will most likely wind up moving somewhere with a less regulated/restricted and more affordable market.

They are negative cash flow as they cannot afford to pay debts and living expenses.

I am worried that transitioning PM companies within a short period of time would fatigue the tenants; however; neglecting a maintenance request would be frustrating for me if I was a tenant. 

In your opinion what are the Pros and Cons compared to more affordable multi-family properties (besides the initial investment size)?

Check out Paula Pant's "Afford Anything" podcast, she answers listener questions in great detail and you can probably find one or more episodes very relevant to your situation.  

But what about a SFH being leased as student rentals, where they typically can't afford their own appliances, and they're used to traveling to laundromats anyhow (or the basement of the college dorm)?

Last, the pre-finished hardwood is pretty affordable when you consider the relative cost of lower-quality products and the fact it is pre-finished so, nail it down and your done.

The type of account would depend on how much you can afford to contribute to it annually.

Short sales can be frustrating, but when they work it is Great!