I'm a haberdasher, so excuse me if I get a bit wordy here!
A simple machine is much better to start on than anything more complicated. If you can get one, an old Jones is fantastic (and pretty much foolproof!). I collect sewing machines and have everything from an antique Singer with boat shuttle to a modern electronic machine, but the more modern ones get much less use than they should. If you prefer a new machine then the JL seems a good choice.
If you are doing buttonholes, then a machine which does single-step buttonholes can be really handy, but even if you don't have that, don't fear buttonholes, they are much easier than they look!
Almost every range of patterns has a beginners range, just choose according to taste and budget. Trace the pattern rather than cutting it out, for two reasons; firstly, it makes the patterns reusable as many times as you want(or you can sell on eBay to get some of the cost back), and secondly, it's easier to change your mind if you realise that you've cut the wrong size, or actually want to add/remove a bit of length etc. There are many fancy pattern tracing cloths available, but I use baking parchment(the kind with a silicone coating) and it lasts for years. Most brands of pattern are fine, but Burda has very, very basic instructions, which matters more for beginners. Ready-to-wear sizing bears almost no resemblance to pattern sizing, and even after allowing for differing amounts of stated ease (the difference between the size of you and the size of the garment), I measure the pattern pieces and deduct the seam allowances, then decide how much ease I need and choose the size accordingly.
YouTube is your friend! As is your local fabric store- it's much easier to get good advice in person than over the internet, and you can feel the fabrics, which is important. Knit fabrics can be tricky, and slippy satins are probably best avoided. Wovens in the right weight (quilting fabrics won't drape well on a skirt, for example) will be a sensible starting place. Most fabric shops have someone who will be happy to advise you.
When I learnt to sew, we only have very old textbooks and the fearsome Mrs Edgington! Now, you can watch videos on youtube, pattern manufacturers websites (Simplicity have a few, as do others) and visit forums or facebook groups. There is all the help and support you could need out there.
Don't worry about pattern weights. Pins are fine, or you can use jam jars, small tins, or anything else you have to hand. I have a very fancy set of metal weights with flamingos on them, but I don't always use them- sometimes pins are easier or more convenient. When you are pinning. start from the centre of the pattern piece. If there is a straight grain arrow, make sure the distance between the arrow and the edge of the fabric is the same at both ends and in the middle, and place pins at those points. Now the pattern will stay still-ish while you work on the rest. It's important to get the pattern as smooth as possible (some people iron the pattern but I don't because of that one time I set fire to one!), but don't worry about that too much.
Two things will really help if you can stick to them; always press (not just iron, actually use pressure too) your finished seams. It makes the whole thing look much neater and will affect how the garment looks whenever it is worn, not just the first time. The second is to try to make a test garment using cheaper fabric in the same weight (often old sheets or curtains, or scrap fabrics left over from other things) before you cut your more expensive fabric. This is called a toile, muslin or calico. It means that you can be sure of the fit, the size and any alterations necessary, and practise any tricky techniques, before you potentially waste expensive fabric. Most people don't make a muslin every time, but it can really help and avoids nasty surprises.
I'm going to stop rambling now! Have fun!