Wow--lots of questions--but I think that's a great thing. Chives. They are a perennial. They won't reseed, but you should be fine in your zone overwintering. If they flower, the flowers are wonderfully edible as well, on salads or whatever, or you can preserve them by drying, making vinegar, or compound butters. I just made a butter with the blossoms and some garlic chives as well that we freeze and pull out to use on corn and veggies. The advice to cut them in thirds is so that you always have some fresh to use. This is if you only want them fresh--you don't have to harvest them. Harvest them by cutting about an inch above the soil line. They can be dried, but chop them finely before drying or you get straw. If you're dealing with small batches and have freezer space, I would just put the stems in a zip bag and freeze them that way--pull and chop and use. Cilantro will bolt (seed) when it gets hot. Collect the seeds too. It does not dry well, and can be frozen, but I tend to not bother because it's so readily available in grocery. I grow it more for the coriander seed which you can get a much higher quality than bought. Cilantro is annual, so you'll need to reseed. You can also do succession seeding next time--plant a small bit, then wait a week and plant a bit more, etc. This way you have different stages and not a huge crop at once. Mint is a perennial. You were right to pot it--it's very invasive. It will come back year after year. I do throw all my containers in a corner of my yard and cover them with straw for the winter to protect them. You can harvest it pretty much any way you want--cut it all off and it will still come back. Or just grab a sprig or couple leaves for tea. It can be dried for tea, or frozen as well in zip bags. When drying, I prefer to strip the leaves first, then dry them. Store whole, and crumble when ready to use. Basil can be dried, but it loses a good portion of its flavor, and has different characteristics once it is. Most people who like fresh basil prefer to freeze it to keep the flavor. You will have to purchase new basil seed next year. You can freeze whole stems or leaves of basil, or you can chop them and freeze in oil or water in ice cube trays. You can also make pesto and freeze that. It all depends on how you will be using the basil. Rosemary will not overwinter for you in zone 5, so you'll need to treat it as an annual, or pot it and bring it in overwinter, but it's a tricky pot plant. Thyme and oregano will return. It really depends how you will be using them whether you want to dry them, freeze them, or just use fresh. Some will say that dried herbs are not worth it, and I agree that badly dried herbs or old herbs like most of what can be purchased really aren't. But it is possible to dry them well for use, though as I mentioned with the basil, the flavor profiles do change, and some like parsley or cilantro truly are not worth drying. I am just learning a lot about drying now, as the Herb Guild I am part of makes gourmet blends to sell at our Botanic Gardens. If you're interested in books, I have one called Homegrown Herbs by Tammi Hartung that I like as a good basic herb book, with both growing and some culinary and medicinal use. It would be worth checking at a library if you can. If you're seriously interested in fancy culinary with herbs, Jerry Traunfeld's The Herbfarm Cookbook is good. The recipes are a mixed bag for home use, but there are a lot of good charts and info on how much of different herbs to generally use.

Are these in pots or in the ground? in your zone the rosemary may not be winter hardy so either bring it in in a pot or cut plenty for drying in case you lose it to the weather. Sage may be hardy for you but dry a supply because it will get pretty scraggy in winter and the smell/flavour will not be as good as in summer. I would pot up some chives but leave some outside too. They will die down but reappear next year. The indoor ones will probably get weak because they will not have their winter rest and may fizzle out. Lemon thyme is less hardy than plain thyme so again I would hedge my bets and put some in a pot as well as cutting for drying or freezing. The basil will die in your winter so freez as much as you can. i have tried getting basil through the winter in a pot but the low light levels have killed it off. I now consider it as a seasonal treat and just grow it from seed each year to enjoy it when it's at its best.

Cranberries are one of those things that can freeze and hold up many years. Also cultivated blueberries. I have some blues my dad picked 11 years ago, and used them last year. Yes they were really bland, but still had a lot of color. Usually when these things dry out and moisture collects inside the plastic bags its due to the fact that the poly bags are not the best protection against freezer burn or drying out, as air amd moisture can pass through. If you want to have fruits last longer in the freezer, a heavier plastic and the removal of most of the air will help. Food Saver bags work great for these things too. Another option is those nice waxed boxes you see that some companies pack veggies into for freezing. Even old half gallon milk cartons work fine too. If possible, even a good freezer paper will also help, if its inside a plastic bag. Those commercial zipper plastic bags for freezers are not the best way to keep things long term. Like you said, maybe 3-4 months at most. I have many string beans left in my freezer from 2006 and they are just starting to show signs of dehydration. Not like that 5 pound box of cauliflour my dad had packed in the bottom back shelf. I pulled it out, and shook it, and heard only tiny rattle noise. Inside the sealed box was a tiny pea side green mass, and it wasn't even 1 ounce in weight. No ice, no nothing, just an almost empty box. Now THATS a dried veggie!

Hard to see from picture, but my guess would be warm moist air leaking from inside the home. Get up there on a ladder at night with garage lights off and inside lights on. See if you can see any cracks at all.