This would be my first wholesale deal and I really don't want to lose this deal.

But really, one loses much more than the $1200 to $1800 when that tenant being upset about rents being maxed out says adios, dude.

An ignorant investment that makes money is still an ignorant investment and over the long term ignorant investors lose.  

Richard: Corelogic provides host of services for mortgage servicers, on of which is monitoring of real estate taxes so that the mortgagee doesn't lose its interest by virtue of a tax sale.

@James DeRoest  to your point I have two good friends in Oregon that went this route against my pleading with them not to .. as I have extensive experience in those markets and with the asset class.. and they did not.one sold a fantastic 60 unit at a 5 cap which is what multi trades for here in PDX these are B's  and bought C class 300 units in Oaklahoma city.. not 8 months later she called me in a panic and wanted to have coffee.. they were ready to lose the building...

In an absolute worst-case scenario, which would I rather lose?  

I got a college degree In business with an emphasis on real estate.  

Emphasis on experience.

On the flip side, cashflow is not nearly as good as some other areas that may or may not be more exposed to the boom/bust cycle.So if you do find a good deal, it will probably be a good deal forever, and it will probably not lose significant value in economic downturns, but the price you pay for that stability is lower cashflow.

it is deductible and some smaller expenses are just not worth losing a tenant over.