1-1. To get the stick to clear spider web, you need to get past the cow furthest to the east, where the entrance to swim in the river is. If you are past Day 6, the cow leaves on its own, opening up the school and old lady's farm in that direction. Continue east, then go up north behind the school. You'll be forced into a bug catching mini-game (I forgot exactly why you want to do it, but it opens up something). Once done, the stick should be in either a bush or tree for you to obtain.
1-2. You actually have to wait on Day 10 to attend a grass mowing event with everyone to clear that area. Once you got to witness it (and claim some freebie snacks, if needed), you can freely go past it for more new areas.
2. Just have to talk to her once a day, and she eventually reveals her painting. I can't remember how many days it took, but best to be persistent with the visits at least 5 days. When you do see the new painting where the blank canvas was, interact with it on one day, then again the next day. On the 2nd day, you'll get the option to masturbate in front of it. You'll later need to have consistent visits with her after that each day, before you can regularly bang her.
3. Ah, the rich lady. Her place is past the long grass, so that's tied to point 1-2 I mentioned above. You will need to meet with Yuu, who's conveniently standing in front of her place and play his paper plane mini-game to get access to her house. The mini-game has two long bars at the top of the screen and the background shows a pyramid or mountain image with you hitting the cursor along it, to determine its speed and altitude (I think).
Your aim is to get an impossible record, which involves your paper plane flying out of bounds really, so you want at least a 90 and 50 to achieve that. So, you might want to save before attempting to do so, as any attempts will pass the time, if you need the in-game hours to do other things. You know you're successful when the conservation talks about retrieving the paper plane past the trees. The rest is self-explanatory from there.
Just to note with Yuu, if you have the BL setting turned off, his next event will not trigger, after beating him in the mini-game. You still get to keep challenging him in the mini-game though at any time, if you wish to.