XP: New Kitten Advice

[more adventurous]

I'm going to XP this on Married Life since I know this board is pretty slow nowadays. 

So, several weeks ago a kitten decided to adopt us (he was squatting in our garage, lol). We tried finding owners to no avail, he didn't have a chip or collar and hasn't been neutered. We decided to keep him. We took him to the vet for shots and found out that he's around 6-8 months. He's bigger...definitely not a baby, but still plays like a kitten. We know literally nothing about cats (so any and all advice is welcome, and sorry in advance for the length).

We have a dog (12 YO female, hasn't ever been around cats much - used to have another dog companion who passed last year) who we're trying to introduce to the cat slowly. We've been keeping the cat in our guest bedroom where the dog can't get to him. We put up a baby gate in the hallway outside of the guest room and at first did some slow introductions that way. The cat could not care less about the dog. Eventually he started hopping the gate (and the dog wasn't ready for that) so we switched to a large wire crate. We'll coax the cat into it and bring the dog in for 15-30 minutes at a time depending on how they do. The dog has super high anxiety but has started to chill out about the cat quite a bit. Usually she'll try sniffing him for a bit, maybe bark once (we remove her and tell her no when she barks), then eventually she'll go and lay down but keep an eye on him. Usually when she starts sniffing him, I can tell she's about to bark so I'll try to break her focus and she'll back off. Yesterday though, I just let her do her thing to see what would happen. She was fine for a while but at some point went to the crate and lunged at him. So, my question with this is, at what point do we decide to let the cat free and see how they do? I don't think that she will ever just completely ignore him no matter how long we do this for, and it's starting to get difficult to keep the cat quarantined. We let him roam when the dog is outside and I think the more he enjoys the freedom, the less he wants to be in the room. (We'll put him back and he'll meow for a good amount of time and has begun throwing himself at the door and trying to figure out how to turn the doorknob, and even lightly bit me once this week when I was putting him back). Any other tips with this?

Part 2 is that we're going out of town next week for Thanksgiving. We plan to move all of the plants and easily destructibles and let him have free reign of the living room/kitchen/his room. We'll be gone for 4.5 days. I'm really concerned that he's going to destroy the furniture and who knows what else simply because we've never left him alone overnight, and he has not had that much space for very long. (Plus he is a very socially needy cat.) The longest we've let him out into the common spaces for is about 30 minutes while taking the dog on a walk. We have friends who have offered to check on him every other day (this would mean him being alone for 1 full day and 2 half days, when we would be going/coming back). Will this suffice, or since it's a new environment should we have someone coming every day? Any other tips here? I also would like to keep him on scheduled feeding so if anyone has suggestions on scheduled feeders that work well (and that your cat hasn't destroyed), I'll take them.

And here's your reward for reading this novel:

[flygirl]

My cat is old so we can leave him from Friday to Sunday with a bowl of food and he’s fine-but I absolutely wouldn’t do this with a new kitten. We hire a cat sitter to come for 1/2 hr each day when we’re gone and it’s only $12 a day. I would find recommendations for this if your friend can’t come daily.
When we got our 2 dogs, we didn’t really quarantine either of them. The cat was full grown and the size of the puppies when we got them though. For the most part the cat ducks out or under something if he thinks the dog is too close. He was also besties with our old dog so it didn’t really bother him to have the puppies come sniff. If you think your dog will bite, I would continue a slower intro.