Welcome, to answer your questions, you can adjust the bag to hang at whatever height you want. Some folks find lower more comfortable, and I like higher. The best thing to do is just experiment and see what works for you. I clip my sternum under the kit bag, and Evan clips it just above the kit bag, and I know another guy who wears it more like a belly holster.
The Alaskan may fit, but I am not sure of that. I know the Delta won't.
One of the most common, if not the most common questions, I get is which size is better for me the Runners/Recon Kit Bag or the Snubby. The short answer is in about 85% of the cases, or more, the customer decides on the Recon/Runners, and in a good number of those cases where they decide on a Snubby I hear back they wish they had gotten the Recon/Runners. There are a fair number of happy Snubby users out there, and hopefully some will weight in, but this is based off the feedback I hear.
I thought it might be helpful to put up the decision making process that I use on those calls/emails.
1. What kind of gun are you looking to carry? If you want to carry something larger than a G19 it is not going to fit in the Snubby, and if it is G19 in size there isn’t going to be a lot of room left in the bag for anything else in the bag. This is my first question, because it is an easy way to rule out the majority of the people.
2. What else do you want to carry besides the handgun? If you want to carry much more than the handgun, your phone, wallet (small and thin), and maybe a spare magazine (for smaller single stacks) then the Snubby is probably not the right choice for you. There are people who do carry more in there and are happy, but in general it is pretty easy to shove enough stuff in a Snubby to turn it into a brick, which is uncomfortable and tends to make it hard to get stuff in and out. You can do this with any of the kit bags, or any bag period for that matter, but being smaller it happens more quickly with the Snubby.
3. Three kind of goes hand in hand with two, but do you ever want to be able to use the Snubby for other handguns or to add more stuff (say for a weekend hike instead of in city use)? Your other handgun may not fit and/or the other stuff you want to add may not fit. The Runners/Recon can be used to carry the same exact stuff, but it will be spread out making the overall package slimmer which will make it feel lighter.
4. How big a person are you? The Snubby excels for smaller framed folks, that and the true pocket pistol/snubbies. I have yet to figure out where the dividing line is because height and weight don’t really have anything to do with it, stature is more its own thing. If you have a smaller chest/torso then the Snubby might make sense, but most folks are going to be above the line where the Recon/Runner will drape the chest better, which provides more comfort. I am not saying that the Snubby doesn’t work just fine for larger folks, but rather the larger bags are going to typically be more comfortable as they fit better.
Uses where the Snubby makes better sense, in my opinion:
1. Smaller stature folks who want to limit what they carry and or have a specific use in mind.
2. Folks who are looking for a dedicated running/cycling bag, which will only be used for a small handgun and limited load out. Frankly, while the Snubby will fit a G19 size gun I think that is kind of pushing it, something more like a keltec or j-frame is a better choice.
This is not a slam on the Snubby, and certainly doesn’t mean that it doesn’t excel in the niche it was designed for, but to point out that it was designed for a niche, and for most folks the Runner/Recon will add a bit of flexibility, and probably be more comfortable. In most cases the Snubby doesn't remain the only kit bag a person has as they find they like it, but are to limited in capacity so they add one of the larger ones for woods use.