Note back to #3, always have exit strategies to handle a variety of situations as they arise.I always like to keep the mindset that the money is made when you buy the property so always track your numbers closely to ensure it pens out when you buy, not a few years down the road based on a gamble.

I would refrain on saying  “to gamble” or something like that.

This is why your post above created several points of information that don't read as accurate.

Hey @Andrew Bailey - I agree with Account Closed said is accurate in regards to rent - if it's in Arbor Hill then good luck and double your expenses because those properties definitely need work.

When determining an accurate ARV do lenders appraise based off the 50% rule or the actual expenses paid in the prior year, IE: tax returns?

When practicing, don't worry so much about becoming accurate with the numbers, be more concerned with learning the process and calculations. 

As long as your Comps are accurate it could be a decent deal, but if the pendulum swings to a $290k sale price, there may not be much profit left.

Should I expect to pay a tax expert to give me a more accurate sense of my situation? 

Assuming that the appraisal is accurate, there's nothing wrong with this.

One thing I really do recommend is talking with an experienced attorney to get an accurate idea of the exposure you face.