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?

The banks that I currently deal with in the U.K. and off-shore do not offer competitive rates for U.S. property.

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.

The next step higher would be to have the holding LLC owned by an asset protection trust with an offshore component.This system has its drawback as it will create some issues for refinancing and will also need a good bookkeeping and operating practice to make sure that you use all these entities in the right way.

It could appreciate but I consider that gambling.

I do sell a lot of the burb investments to my off shore buyers because that is what they want, but I like inner city more. 

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.