A lot of major universities have a farm extension service. They give really good advice not centered on selling you stuff.
So when you search on something like fruit tree pruning (or any other topic you can imagine) and see an address like
https://extension.umaine.edu/...es-in-maine/pruning/ - use those - they will essentially teach you how to farm.
It sounds like a lot of what you are looking at is around fruit trees. Spray - on time every time. Especially the early season times before the fruit even sets on. My dad has always told me that they used to say when the last drop of rain hits the first drop of spray should hit. Yeah, I'm not doing that. But if you don't spray properly your yield will be low and your fruit will look like shit.
Pruning is as much art as science. If it looks good to you aesthetically it is probably pretty close to correct. Apple trees are really resilient around pruning so if you make mistakes they will recover.. It will probably take a couple years of pruning and thinning to get neglected trees back to being good. Be willing to remove large branches if it is called for. Be careful to not just whack it back to only big branches because then next year it will just be a brushy mess. It is hard to wrap your head around how much you should thin them out. I continually leave too much, and it reduces yield. Another dad'ism, you should be able to throw your hat up and have it fall through the tree without getting stuck. Again, an overstatement but take more rather than less.
Grapes can depend on the variety if they form on new or 2nd year growth. But you can and should prune them way back every year.
Blueberries I have never trimmed. I keep the weeds and brush out of them, spray them when I spray everything else (but I'm not actually sure they care) and pick the bejesus out of them every year - by far the easiest to care for
I'm assuming you have your own cider press - hard to find anyone around here to do it for you any more. Clean it. Really well. If you don't, the next batch will start working really quickly from the leftover yeasties eating the leftover apple parts. Use good clean apples, pick out the rotten ones and don't let mud in or else, remarkably, your cider tastes like rotten apples and mud. 3 gallons to the bushel +/- is what we usually see.
That is a LOT of trees. I think the most we had growing up was 15 - 20. The pruning will take a good bit of work and needs done while they are dormant, I would not think any worse of you if you picked out the trees and varieties you liked and pruned the rest about 3" tall with a chainsaw :) And 29 trees can produce insane amounts depending on whether they are dwarf, semi-dwarf, or full size. You could be looking at 4 - 500 bushels of apples out of 29 full size trees (and that many dwarf can easily be 100+). Not sure how many apples you have picked in your life, you do not want to pick several hundred bushels of apples yourself every year. I usually prune in very early March in OH. Sucks to be climbing in the top of trees in cold rainy wind and I have to do my dad's too since we don't let his 94 year old butt climb trees any more.I've got 4 apple, 2 pear, 2 cherry, 2 peach, 2 plum, along with blueberries, currants, grapes, and strawberries and the gardens.
The only winter prep I do is make sure all the weeds are trimmed down, cover the strawberries and roses, and do any projects on equipment.
I'm way into my gardens and fruits. I grew up on a farm and I think I probably made a mistake in not making it my career. I'd much rather talk roses, blueberries, strawberries, and apples than politics.
I'm beginning to think that we are much more fucked than I thought.
That’s a good girl there. Looks like a sweetheart. 
