i'm not an outliner, but i take tons of notes. at some point those get written as scenes as interest allows and them put into some kind of order. so, i'll have lots of connecting the dots to do. the one thing i don't do, however, is not know what the ending is. in fact, i'll usually do the ending pretty early on. and i work retro-fitting everything to match the ending.
i've said it before many times, if you know your ending, you should be able to deduce your beginning. everything between those two points is justifying how that change occured. i think that's true even in *good* plot-driven stories.
i learned early on that i didn't care for outlining too much, BUT meandering aimlessly wasn't getting it. in other words, i really didn't want to continue asking the same questions you asked, so i found a way i could live with that alleviates those questions if not obliterating them outright. the solution to my problem was working backwards and skipping around in a lot of respects (this is particularly true for me as when i skip around, then i know what characters need to be in the beginning), not sure what your ultimate solution is. i have to say i 'wing it,' though i have my gameplan set.
of course, in the course of justifying the end with its beginning, i do like to go off on tangents. that's the fun part for me because it's challenging, and that's usually the ACT II stuff. i'm not sure how true this is, but off the top of my head i'd say people who don't actually enjoy writing the middle stuff lacks the kind of focus that knowing what your ending will be provides. and not just a kinda/sorta ending-like-esque type of wishy-washy maybe/maybe not roundabout thing, rather something you entirely expect to end the story with barring your muse doing a jig on the creative impulse centre of your brain at the eleventh hour.
bear in mind that it's not too late to outline the last quarter of your story. that possibly might help. it sounds to me like you don't have a clearly defined direction and goal. is it common for a first draft? i'll put it to you this way ~ probably not for professionals. i'd venture to say most pros get tired of stumbling around in the dark hoping to trip across their answers, even the ones who claim to 'wing it.' a professional knows how precious their time is and will want to work as effectively as possible. that's what makes them professional and not a hobby writer who gets lucky every now and then. i doubt there are an abundance of professional novelists out there who make their living writing with the attitude 'oh, i'll fix it in the fourth or fifth draft.'
that's probably why i don't like the 'just write it' advice for anyone other than rank amateurs. i will *always* aver that you should write it as well as you possibly can the first time just like i'll always say don't start your research 75K words into it.
you hear of some writers who won't put out anything less than eight drafts or something ridiculous, and it always makes me wonder why the hell they need that many. i mean, what could possibly be that different between draft four and five? but six and seven?! unless you call running it through spell check three times three drafts, i simply can't fanthom the need for it.
muddle through this one the best you can. but for the next project, i'd suggest taking up what i consider a professional stance and know where you're going before you get there lest you get lost in the process. it's probably happened to everyone, and to some extent probably professionals, just that without a plan of attack (which you're experiencing right now and how fun is that?) your chances of missing your mark are a lot higher, eh?
then again, i believe the term 'wing it' is misleading. i'd have to say, given the choice of 'outline' or 'wing it' that i fall in the latter category, but it's a lie. i take notes. i jot down scenes and ideas. i fall asleep thinking about the story. i think about it at work. if i didn't have a stand up job i'd probably fall asleep at work thinking about it. hardly pulling ideas out of thin air. once there's some clear definition, i know the ending. i know the ending, i know the beginning. everything between is just fun/interesting/cool/actiony/dramatic shit to get from point A to B. i do it this way to prevent myself from writing twenty thousand words more than i have to, then re-tooling major sections after 'the end' to make it fit.
were i ever to send in something for publication, i'd expect the editor to expect me to show some professionalism, and i hardly consider 'winging it' in the true sense of the term desirable for anyone. i certainly wouldn't want to be in the practice of 'winging it' if ever there were deadlines to meet and here i am without a clue as how to manage my time for a damn, know what i mean? in any other professional you'd be fired and rightfully so.
'well, not everyone does it that way, preyer!' true. some people write just to get the ideas out. and waste a shitload of time in the process, imo. that is, if this is your approach, just write a damn outline and save yourself a draft. that's assuming that this whole writing thing isn't completely alien to you, of course.