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A boy with a winning smile, two grandparents hosting him for a sleepover – all three are missing and their loved ones fear the worst.

Nathan O'Brien and his grandparents, Alvin and Kathryn Liknes, were last seen around 10 p.m. on Sunday, June 29, when Nathan's mother left her parents' home, where she had been helping them operate an estate sale. Nathan was supposed to sleep over.

Jennifer O'Brien returned to pick up Nathan at 10 the following morning. The house was empty.

More than two weeks have passed with no sign of the missing trio. An intense police investigation has yielded, in the words of a spokesman this week, "more questions than answers."

A man who has a family connection to the missing trio has been called a "person of interest" and was questioned by police while being held on an unrelated charge. He was released on bail Friday, but is back in custody again.

The rural property north of Calgary where the man was living in his parents' home was subjected to an intense police search last week. Investigators have also searched two landfill sites.

Here are the key questions hanging over the case:

Calgary Police Service

1. Who are the missing people?

Nathan is five years old. Said to be fond of superhero characters, he stands three feet tall with blond, curly hair and brown eyes. He was last seen in peach shorts and a striped blue hoodie.

Mr. Liknes, 66, is about six feet tall, weighs 200 pounds and has grey-blond hair. He has a distinctive walk. Ms. Liknes, 53, is five feet, three inches tall, weighs about 120 pounds, and has red-brown hair and green eyes.

Police have said there are no issues of child custody in the family. The boy’s parents, Jennifer and Rod O’Brien, are married and he is their biological son. The Likneses do not have any known enemies, Ms. O’Brien said. She would not say whether there were valuables left in the house.

The O’Briens live in Calgary and work for Cenovus, one of the country’s largest oil sands producers. They have three sons.

“Your whole family loves you to every star and back,” Mr. O’Brien said, addressing his missing son, at a news conference last Wednesday. “Nathan, you are our superhero right now.

“Mom and Dad need you to be brave right now. To whoever has Nathan, please find it in your heart to drop off our little angel, Nathan, to which he can be rescued and reunited with his brothers and his family,” Mr. O’Brien said, holding a colourful paper butterfly the boy had made.

“Nathan, we love you big. We will see you soon.”

Jennifer O'Brien holds a piece of her son's clothing while speaking to the media about her son and his grandparents during a press conference in Calgary on Wednesday, July 2, 2014. (Jeff McIntosh/The Canadian Press)

2. Are they still alive?

As the search for the trio continued on Thursday, police did not disclose any ransom demands or other communication from the alleged abductor or abductors.

Given the circumstances, it would be unusual for one person – let alone three – to be found alive after disappearing so long ago.

In addition, investigators have said that violence was involved in the case. “A violent crime occurred in that residence,” Staff Sergeant Doug Andrus said. “Based on the evidence, I would say that somebody would be in medical distress.”

Extended family members have said that while they are still hoping that Nathan and his grandparents will be found alive, they believe that the chances of a happy reunion are dwindling.

“We’re just hoping for the best, but kind of fearing the worst,” said a relative, who did not want to give her name.

Police investigators prepare to search a hay field north of Airdrie, Alta., Monday, July 7, 2014, looking for clues in the disappearance of five-year-old Nathan O'Brien and his grandparents. (Jeff McIntosh/The Canadian Press)

3. What evidence has been found?

Police have been selective with the information they release, but they did say early on that there were signs of violence in the home and its condition was “inconsistent” with the couple’s habits. Staff Sgt. Andrus told reporters that there were “marks” on the side of the home that run “a distance.”

Yet police found no signs of forced entry to the home. Was a door left open, did someone enter with a spare key, or did the Mr. or Mrs. Liknes open their door to danger?

Their vehicles are accounted for, as are those of the rest of the family. Border officials were notified, but this did not generate any leads, police said.

Police removed evidence for examination from the Liknes home, but they have not described it in public.

They also removed items from the rural property that became the focus of the investigation last week and sent them to the crime lab, a police spokesman said.

Two landfill sites were searched on Wednesday and Thursday, but police remained on and around the rural property near Airdrie.

Calgary police investigators check out the home where five-year-old Nathan O'Brien and his grandparents Alvin and Kathryn Liknes disappeared, in Calgary, Alta., Wednesday, July 2, 2014. (Jeff McIntosh/The Canadian Press)

4. What is the significance of the estate sale?

On the day before their disappearance, Mr. and Mrs. Liknes held an estate sale in their home. They had sold the place a year earlier and were leasing it back, but were planning to move to Edmonton (and take an extended vacation in Mexico).

Between 200 and 300 people went into the home during the sale, which featured many common household items, according to people who visited.

Nathan and his mother were there to help. The boy reminded his grandmother repeatedly to say “thank you” to people who purchased things, his parents later said.

The estate sale was advertised on the online classifieds system Kijiji. This led some observers to suggest a scenario in which someone with criminal intent may have noticed the sale and targeted the home.

More to the point, the presence of scores of strangers going through the home a day before a probable crime creates an enormous headache for investigators trying to learn who entered the home later that night.

Staff Sgt. Andrus said police dusted for fingerprints – which must have been numerous – and are trying to compile a list of what was sold against what is missing from the home. They asked citizens who attended the sale to bring photos of items they purchased to a community hall in southwest Calgary, and were also asking for fingerprints from these people.

In this artist's sketch, Douglas Garland appears in court in Calgary on Monday, July 7, 2014. (Janice Fletcher/The Canadian Press

5. Why has one man been singled out as a ‘person of interest’?

Police took Douglas Garland, 54, in for questioning related to the missing-persons case last Friday. They later released him, but then arrested him on an identity-theft allegation dating back nearly a decade. He was released on bail Friday before beign brought back into custody on Monday.

Earlier, police released an image of a green Ford F-150 pickup truck, saying it had been spotted several times on the day of the disappearance.

Soon after the image was made public, police went to the rural property owned by Mr. Garland’s parents, where they said a truck found on the property matched the one in the surveillance video.

Mr. Garland, who is 54 and lives with his parents, has a close connection to the Liknes family through his sister, Patti Garland, who is in a relationship with Mr. Liknes’s son, Allen, according to a relative.

Investigators have questioned Mr. Garland in relation to the mysterious disappearances, but he has not been charged in relation to the case.

Mr. Garland has a police history, with past charges relating to drugs and identity theft, and has served time in prison.

With reports from Carrie Tait, Anqi Shen, Jill Mahoney, Allan Maki and The Canadian Press