He does not try to hide his disappointment that things have not gone better but is satisfied brighter times are ahead for him and the team, feeling that improvements in the understanding within a new-look squad have been made.
Whether he has been playing golf at The Wynyard Club, on the estate where many of the Boro squad live, with a number of his teammates, or sharing lifts with Stephen McManus, Willo Flood and Lee Miller, Bailey feels at home.
It can't have been easy for the man from Hammersmith.
Prior to his move to Teesside, he spent time with Sutton, Barnet, Southend and Charlton, meaning he never had to leave his West London roots.
He chooses not to make his switch to the region as an excuse for early-season frustrations, but does accept he now feels more familiar in his surroundings, particularly on the pitch.
If you are a strong person then you don't let things like that affect you he said.
I am like that, nothing really affects me. I'm sure it does affect others more but I don't put my performances down to the move.
I do have plenty more to offer, of course I do.
But it has been more a collective thing. As a team we have to gel together more.
In the last two games we have put in two decent performances so, hopefully, there is more to come.
Bailey would have liked the chance to experience more of the region, but has found he has not had the time he would have liked, juggling training and matches with looking after his three young children, Maisy, Tilly and Archie.
He has a fourth on the way in December.
I have a family now. I am not as outgoing as I used to be, so it is nice up here for us, it is quieter, but that is something you have to get used to,
said Bailey, who has spent his life living in Hammersmith and Putney.
In London it is all in your face and you can't get away from it. Everything is full throttle. You can still go out and do the same things but everything up here seems to be a lot cheaper than it is in London. That can only be a good thing for me.
Bailey missed the win over Burnley last week but returned to the fold to help defeat Reading 3-1 seven days ago. He is, though, keen to head to Watford today and continue that run, with a healthy following watching him.
At QPR I needed about 20 tickets so it was disappointing to lose 3-0 like we did, he said. I try to get as many as I can and I have about ten coming to the Watford game.
There is an extra incentive for me to show my friends that I can play well for Middlesbrough so Watford is the next game for me to look to.
Having said that, my main mates have been coming to all of my games this season.
They are good like that.
My dad likes to go to the closer games. You want to play well when you are down there and you have your dad watching.
Preston manager Darren Ferguson is confident his side can turn around their poor start to the season, starting with today's npower Championship trip to Coventry.
North End have picked up just one win from their first seven league games, over bottom club Portsmouth, and are on a run of five-straight defeats following their midweek Carling Cup reverse at the hands of Barclays Premier League side Wigan.
Ferguson will watch from the stands at the Ricoh Arena as he serves the last game of a three-match touchline ban he received for his conduct towards referee Kevin Friend following his side's 4-3 derby defeat against Burnley.
But the Scot said: Myself and the chairman are determined to turn things round.
There are many examples of other teams who have been in our position and turned it round.
Source: Northern Echo
Source: Northern Echo