@Caroline Gerardo In regards to the 6% commission eating all the LTCG tax, from my research I was under the impression that only the 6% commission would reduce the amount taxable, i.e. reduce the $113,000 down to $95,230 - decreasing LTCG from $16,950 to $14,285 (15% of $95230)?

I am interested to know if deeding a property from one land trust (with one LLC as trustee for flipping deals) to another (with a different LLC as trustee for buy and hold) is a taxable event.

However, if you don’t follow the rules, you could purchase a property the wrong way, disqualify the IRA, and create a taxable event.

@Dave Foster Many people are unaware that they can also 1031 into a trust instead of a physical property... so in the event that the "like kind" property exchange is not going to go through, they can defer paying taxes by moving the taxable income into a trust. 

@Roman Capone, any money you take out of a 1031 exchange is going to be considered profit and will be taxable.  

Moreover, it sound like you live pretty close to the property, so you might even be able to cut that number down by doing some of the repair and maintenance yourself.I would look concretely at what the taxes would be upon a sale (it looks like you're a realtor so check out what the current taxable value is on the property by looking at the public record), speak with an insurance agent about what they might charge for a premium on this property, and gauge how many repairs you would need to do in the next 1-5 years.That's where I would start if I were looking into this deal.  

(if he wants to control when earnings are repatriated to Canada, then he's looking at incorporating an entity in the U.S.)The best advice for him is to jot down his situation and objectives in point form, then find both and accountant and attorney who have cross-boarder business and real estate experience and spend a few hundred dollars to find an ownership structure which fits his immediate needs, but that will grow with him, or can easily be transformed to meet is longer term objectives without creating a nightmare of taxable events.

The improvements done by the HOA could increase the taxable liability of the condo if the tax assessor thinks it does. 

You have 60 days to get those funds or assets back into another retirement account, or it becomes a taxable distribution to you.  

Your guys' assumption about the commission is pretty much as far away from the truth as saying - "a cash out refi is taxable income because you have money in your pocket after the refi."