First, I'd like to say what a fantastic site and community this is, and how helpful it has been! Here's our story 
Mr. Bootz was a feral kitty living in our backyard in a neighborhood with several community cats, but he was particularly friendly so much so as to even coming inside of our enclosed patio and snoozing behind furniture in there.
His extended visits combined with the fact that he seemed to be frequently bullied by other cats made us decide to trap fix and bring him inside. (We also tnr'd another much more feral cat and intend to tnr the colony further) To our surprise the vet estimated his age to be under 1 year, which encouraged us further in our endeavors, hopeful that a younger kitty would adapt faster and better enjoy indoor life. Upon moving mr. Bootz in we provided him with a small room of his own including a cat tower, hiding spaces, toys, a litter box, automatic dry food feeder Etc. Unfortunately there was also a couch in this room which we failed to properly block off so he soon discovered his favorite hiding spot under the couch. For the first couple of weeks he was extremely shy and skittish and we rarely saw him. He mostly only appeared to eat sleep and use his box (he gets wet food daily in addition to his dry food). However he increasingly became more confident in our presence and we elevated the couch so that his previous hiding spot was not as hidden (though not gone), forcing him to further socialize or at least acknowledge our presence. He still retreats under the couch, but is not hidden. I should mention early on we frequently left his room door closed, but have gradually been leaving it open more and more when we are home. Around this time we had our first meows as well. It is now been nearly two months and mr. Bootz’ routine has become to sleep, eat, cry at the window, play with his toys, play hunt, groom, and in the evenings explore beyond his room some. He still will not let us touch him, however he made physical contact with me for the first time a couple days ago, pressing his nose against my arm after eating some treats near me. I am confident with more time he will become more comfortable with physical interaction. I am able to engage him in some play with a wand toy, but frequently see him play hunting and pouncing on his stuffed mice and feathered toys when I'm in the other room. Early on there was extensive evidence that he was climbing curtains in the room however that seems to have subsided as he has found good access to the window.
Given his progress I have been encouraged and feel I made a good decision bringing him in, however in his bouts of crying at the window I often feel incredibly guilty. The upside is this behavior only seems to last for a few moments at most before he is back to grooming or playing with his toys.
Unfortunately, we had a scheduled trip out of state for 10 days in the coming week. We've hired a pet sitter to come daily and cycle his food, water, and chat with the kitty for 20 minutes or so. In addition we have a friend of the family stopping by occasionally. I guess my biggest concern is that our sudden absence and introduction of new faces could be further traumatic for the kitty. Additionally he is not ready for a full household access yet unattended, so he will spend the 10 days in his Kitty room the size of a small bedroom. I plan to leave items that smell like me in the room and provide the cat sitter with new toys to provide intermittently during our time away. Additionally he has an automatic feeder and some interactive toys as well. I feel guilty (massive anxiety as well) leaving him in a confined space, however I have tried to provide him with as much enriching items as possible. I suppose why I'm writing is in hopes of eliciting suggestions or advice to further ease any stress he may feel in our absence.
Thanks for any suggestions,
Rob (crazy old cat man in training)
Mr. Bootz was a feral kitty living in our backyard in a neighborhood with several community cats, but he was particularly friendly so much so as to even coming inside of our enclosed patio and snoozing behind furniture in there. 
His extended visits combined with the fact that he seemed to be frequently bullied by other cats made us decide to trap fix and bring him inside. (We also tnr'd another much more feral cat and intend to tnr the colony further) To our surprise the vet estimated his age to be under 1 year, which encouraged us further in our endeavors, hopeful that a younger kitty would adapt faster and better enjoy indoor life. Upon moving mr. Bootz in we provided him with a small room of his own including a cat tower, hiding spaces, toys, a litter box, automatic dry food feeder Etc. Unfortunately there was also a couch in this room which we failed to properly block off so he soon discovered his favorite hiding spot under the couch. For the first couple of weeks he was extremely shy and skittish and we rarely saw him. He mostly only appeared to eat sleep and use his box (he gets wet food daily in addition to his dry food). However he increasingly became more confident in our presence and we elevated the couch so that his previous hiding spot was not as hidden (though not gone), forcing him to further socialize or at least acknowledge our presence. He still retreats under the couch, but is not hidden. I should mention early on we frequently left his room door closed, but have gradually been leaving it open more and more when we are home. Around this time we had our first meows as well. It is now been nearly two months and mr. Bootz’ routine has become to sleep, eat, cry at the window, play with his toys, play hunt, groom, and in the evenings explore beyond his room some. He still will not let us touch him, however he made physical contact with me for the first time a couple days ago, pressing his nose against my arm after eating some treats near me. I am confident with more time he will become more comfortable with physical interaction. I am able to engage him in some play with a wand toy, but frequently see him play hunting and pouncing on his stuffed mice and feathered toys when I'm in the other room. Early on there was extensive evidence that he was climbing curtains in the room however that seems to have subsided as he has found good access to the window.
Given his progress I have been encouraged and feel I made a good decision bringing him in, however in his bouts of crying at the window I often feel incredibly guilty. The upside is this behavior only seems to last for a few moments at most before he is back to grooming or playing with his toys.
Unfortunately, we had a scheduled trip out of state for 10 days in the coming week. We've hired a pet sitter to come daily and cycle his food, water, and chat with the kitty for 20 minutes or so. In addition we have a friend of the family stopping by occasionally. I guess my biggest concern is that our sudden absence and introduction of new faces could be further traumatic for the kitty. Additionally he is not ready for a full household access yet unattended, so he will spend the 10 days in his Kitty room the size of a small bedroom. I plan to leave items that smell like me in the room and provide the cat sitter with new toys to provide intermittently during our time away. Additionally he has an automatic feeder and some interactive toys as well. I feel guilty (massive anxiety as well) leaving him in a confined space, however I have tried to provide him with as much enriching items as possible. I suppose why I'm writing is in hopes of eliciting suggestions or advice to further ease any stress he may feel in our absence.
Thanks for any suggestions,
Rob (crazy old cat man in training)
