This that I read here, it's not investing, it's gambling.

Timing the market is like gambling. 

I'd get a good handle on risk tolerance so you're investing rather than gambling.   

This is a 1 bedroom condo that does not make sense to rent out.Purchase price: 390kRehab: 30kCurrent value: 485kWhen I say 485k, I mean that if I put it on the market for that price today then it would have 10 offers for that price within a day.So the main question is:Do I sell it now and pay the higher taxes on the sale, or do I gamble with waiting till October to avoid paying capital gains taxes?

investing in real estate should not be as hard as investing in the oil and gas industry, when folks digging a new oil well, everyone knows they are gambling 100%. real estate investing has to be seamless and everyone should work together, including the buyer and seller, you're not buying a gold mine here so the reward/risk ratio is not there, and you may see only the pain.

@Shiloh Lundahl Yup, all for market inefficiency at time 0 :)  not gambling etc. 

Flying below the radar—otherwise known as trying to be invisible and hoping the city never finds out your property is a rental—can ultimately be an expensive gamble.

It could appreciate but I consider that gambling.

Waiting for appreciation that might not come the way you want is a big gamble. 

@Jimmy Woodard the city is built on tourism and gambling revenue.