Gamble: Quote from @Clinton Jensen: Thank you for your reply @Timothy Maloney1.

For this rent value you'd want it to be something like $170k and lower OR have a much higher appreciation rate (which is akin to gambling and not investing since it is a bet on something happening in the future in order to make sense as an investment).Surely the NET rent is what is taxable. 

Do you really want to take that gamble in court? 

This is investing not gambling.

Yeah, auctions in my opinion can be a little bit of a gamble and you only get the deals when someone doesn't show up to outbid you so you aren't controlling your lead flow.

If so, is it just a gamble in hoping you don’t get caught?

Don't want to catch yourself gambling on a bet that wont pay out

After a 5 year holding period, you may be able to withdraw your basis from the Roth tax free to purchase more real estate (note, I need to verify this as I don't know this to be 100% accurate)- You could potentially offset taxes from a year where you anticipate large gambling income, cancellation of debt or more likely, stock option awards or other employee stock incentives. 

Speculation is somewhere between investing and gambling.  

It's a calculated gamble, betting on the resurgence of office spaces and the city's magnetic pull for businesses.However, with high stakes come high risks.