Even if you find a multi family that will cost you 100$ a month after the other side is rented (in my opinion) that's still a win for your first property while you save a ton of money to purchase another property.

I would simply add a second, or third, or fourth mortgage on a property as my commission.

My question: do I send a general letter simply stating that I'm interested in purchasing the property & request that he call, or do I mention the tax delinquency & let him know that I'd like to help him solve this problem.

You could work on some flips, try to find partners with money, or try to wholesale but simply purchasing cash flow properties may delay your goals of buying a property like that. 

Link. Short article.TLDR: If an Oakland landlord is fined/penalized due to the condition of a rental property, and appeals it, the folks that issued the fine will no longer be the very same ones reviewing the appeal. ...

On average you can expect to pay upwards of $1000 to acquire enough leads to close a deal.So with such a small monthly budget how would you win with paid traffic?

Now, I don't begrudge anyone from making a living, and I always seek to create win/win business relationships - but honestly I could quit my high-income white collar job and bill myself out for snow shoveling and gross more income if people are paying these prices in the bids.  

Any thoughts how I can make this into a win win situation?  

They simply can not find a better product for the same price and so they stay.

Just simply refi the investment property...estimated balance with all costs rolled in $110k = $590/month P&I = $1702/MONTH TOTAL between two mortgages (-$100 in cash-flow compared to option #1) (5% rate for investment property)