Residents expect it and it does reduce time on market.

Ditto for reducing Police or Education expenses to the degree necessary to effect real change.Here's a link from DNA Chicago specifically discussing how the property tax increase will gentrification in these neighborhoods.  

If so you're far less likely to default and lose your home so that shouldn't be much of a concern... worst case you can refi (even at a higher interest rate) and reduce your payments. 

If they come dinged or scratched I can take it back to the store or get the company to give me the item at a reduced price. 

This strategy has worked well for the both of us as it has allowed her to continue her "main full time" job and it has significantly reduced my expenses.Hope this helps. 

As far as not renting for what you're told it will rent for, you can reduce that risk by only working with a turn key company that places the tenant before you close then you don't get any surprises. 

Best is to be pro-active and look up a few hard lending topics and members here on Bigger Pockets and ask them directly how to handle your current situation.

Possibly get a slightly reduced price.

This is not tax advise on your particular return but some things to discuss with your tax professional.When you say underwater are you reducing the shortfall by the monthly Principal Payment that increases your equity in the property on a monthly basis?

I want to stay in the high end market in order to maximize the cash flow per deal and reduce the amount of total property management required.