If @Mitchell Morwood flips the property he grosses $100K ish and after taxes makes $60K ish because he'll pay ordinary income tax, self employment, ACA surcharge etc. 

Anything out the ordinary I should look out for?

Selling at less than a year will have you paying ordinary income on the profit which will be much higher and will also include self-employment and probably the ACA 3.8% surcharge. 

Besides, any depreciation deduction is recaptured when the asset is sold, albeit at a lower tax rate than the ordinary income that was offset by the depreciation in the first place.Another important consideration is that an investment yielding a 2.0 multiple isn’t necessarily a better investment than one yielding a 1.4 multiple.  

In reality, the cost basis gets adjusted by different expenses/renovations/depreciation you may have made to the property and the sale price gets reduced by certain expenses ... but let's not complicate this for right now :)  Key thing to understand, though, is that doing a refi doesn't change your cost basis.You paid $209k and sell for $300k ... that's a $91k gain that you will be taxed on - the Fed will treat it as long term capital gains - depending on your state, it will likely be taxed as ordinary income.If you've lived in the property as your primary residence for 2 out of the last 5 years, you can shield the entire $91k from being taxed. 

This is not an ordinary appraisal and most appraisers won't understand all of the issues present.

That's taxable income at ordinary rates, plus you'll owe self-employment tax.

@Robyn Smyles it probably doesn't matter because it is taxed as ordinary income so it drives your total income up. 

You'll pretty much just be earning ordinary income. 

I think you are looking for a "Fee only financial planner" - your instincts are great, this is a thing, and you are wise in my opinion to be skeptical of traditional financial planners, who WILL try to sell you in many cases on expensive whole or universal life insurance (VERY rare use cases where this is profitable to the ordinary investor) and/or will charge fees for Assets Under Management.