I might be repeating some stuff others have already said, but having always been a multi dog house-hold, I wanted to share my experiences as well.
1. Taking walks... best tips for walks with two dogs- especially one tiny? Do you suggest those like leash splitter things?
I wouldn't walk them together currently. Wait until both dogs have good leash manners before you walk them together. Walking them separately, although kind of a pain sometimes, is also a good opportunity for some one on one time for you and both Jude and Jonah. And when you are able to walk them together at some point, I recommend two separate leashes. I really don't like coupler leads. They get in the way, and I just find them irritating. I prefer the control of having a leash for each dog should I need it. With a coupler, should something happen, or if one dog is faster paced than the other, the outcome just generally isn't good.
2. Car rides... what do you do for your dogs? Jude sits in the front now. Ideally I want them both in the back in seat belts, after someone hit me from the back this year and I was so relieved Jude wasn't in the car- but do carseats really work? My dogs will be in the car almost every day.
I prefer all dogs to ride in crates for safety reasons, but I understand it's not possible for everyone. Our car is too small for three crates the sizes we need, and so Keira and Dance ride in the backseat (generally free, but they do have seatbelts -- they just manage to get all twisted up in them somehow though) and Ripley rides in the very back if we're taking all of them together somewhere.
3. Bowls and eating- do you put them near each other? Do they share water in the beginning? Do you feed the older dog first? How can i encourage Jude to not finish his food and go over and try to steal Jonah's food other than reprimanding him?
My dogs always share water, and I feed them in close vicinity to one another (different corners of the kitchen), but not side by side. I tend to feed in the order the dogs came to us (so Dance first, then Keira and then Ripley)... they don't really care in which order they eat though I don't think. Sometimes the Dobes' order gets turned around, and nobody complains. And if Jude tries to steal Jonah's food (and vice verse), tell him to leave it alone and redirect back to his own bowl.
4. New puppy and older puppy... did it work out putting the little puppy in a crate? I think that's my plan. Jude likes to sleep in the living room. Would you put Jonah in the living room in a crate or in with me?
I'd put Jonah in a crate in your bedroom for now. You want yourself to be the one to comfort him (not coddle, but you want him to know you're there if he starts fussing in the night) those first few nights he's home, and I think he'd be happier being with you than alone in the livingroom with Jude.
5. When I want to clicker train the new puppy- should I give Jude something to do? Raw meaty bones and kongs outside? Or should I teach him he needs to lay and watch. He has a really hard time with this at agility classes. Tips?
I either put my dogs in a wait while I work with another, or send them to another room. When I work with an individual dog, I don't want the others crowding us. You can definitely give Jude something else to do of course. Just don't have him getting in the way of Jonah's sessions.
6. How do I not feel guilty!!! I want to bond with Jonah like I did with Jude- lay with him in bed sometimes- hug and kiss him- but I feel so guilty...
Honestly, I find it really hard to get the same close bond with a second dog as you do the first. Simply because there is more than one dog to focus your time and attention on now. It is possible though, and you just have to make sure when you want some one on one Jonah time, that Jude doesn't shove his way in. And when you're done with Jonah, it can be Jude's turn. When you have multiple dogs, one dog can't be the centre of attention all the time -- it's impossible. But when you say so, one dog can be the centre of attention some of the time. It's all about balance, and you don't have to feel guilty.
7. Toy sharing... Jude is very much an only child. Anyway to make this easier?
Don't expect them to understand the concept of "Jude's toys vs. Jonah's toys". I don't leave a bunch of toys out for my dogs (because they wreck them all, so I only bring them out for playtime) aside from Nylabones and Kongs, but they're all good about sharing them. If one dog is chewing a bone and another tries to steal, I do allow a little warning growl from the chewer (it never escalates and only happens when the other dog is being rude). Another dog shouldn't be allowed to walk up and steal something right from the other dog's paws or mouth. And if the other dog persists, I tell him him/her to leave it alone and try redirecting to something else. In my home though, it seems that what one dog has is what the other will always want. I have all sorts of bones and such laying around the house, but Ripley will sit and wait and not chew or do anything at all until Dance is done with her bone. And when she walks away, he'll take that one. I don't allow resource guarding, and none of my dogs do resource guard. They're allowed to communicate nicely to another to back off if they're being rude, and for the most part they work things out just fine on their own. Sometimes they do steal from one another, as most of the time my dogs won't say anything, in which case I'll take the bone back from the thief and give it back to the dog who originally was enjoying it (and try giving a new bone to the thief).
8. Any other overall tips... this is all foreign to me. I've never had two dogs before- nevermind an older puppy and a little puppy. I'm so excited- but in completely new territory. All of your advice is so, so appreciated.
The biggest thing I feel is important in multi dog ownership is not to let your dogs become dependent on one another. A friendship bond is good, but I don't want to see a dog become totally attached at the hip to the other dog. My dogs are all friends. They play together, they sleep together, they enjoy eachother's company. But they do not care if one goes somewhere without the other, they do not care if one leaves and doesn't come back for a while, etc. They like eachother, but their people (mom and I) are the most important things to them. I want my dogs' bonds and relationships to be stronger with humans than the other dogs in the home. So I make sure any new puppy I bring in has a lot of one on one time with me and that the other existing dog is not always with us. I take them separately for walks, I play with them outside separately, I'll even put the adult dog away for some alone time in the house with a puppy. Not enough that the first dog/s get jealous or to the point where I feel guilty about not spending enough time with them, but I do feel it is very important for a puppy to have quite a bit of time alone just you and him/her. I know a lot of people who seem to get a dog for their dog, rather than another dog for themselves who will also be the other dog's friend. And alternatively, I will also crate the puppy so he/she can have some quiet time (and it's good for crate training anyway), and have some alone time with the adult dogs.