You have to start somewhere. There are lots of unknowns, lots of marketing to wade through, and be prepared – you will NOT get everything right without correcting mistakes, but in order to correct mistakes and learn from them, you first have to make them. And if you do, you are honestly on the path.
1.Get oriented.  Figure out as much as possible what you want as best you can, even if you are brand new and haven’t a clue  As you learn you will redefine LOTS of things, but for now, orient yourself as best you can with the information you have at hand – right now.
Doing this is actually starting ‘the planning process’ which will later prime the pump for decision making, e .g  the combat estimate and other processes. Go ahead and substitute other words: aim, goal, objective, mission. The point is to have a defined focus, and focus means there are boundaries and limits, If you defend everywhere, you defend nowhere. That’s not to be negative, but it’s to prevent chasing your tail. Do you want to focus on ‘general preparedness? Some part of that, e.g. communications, tactical? Skill acquisition? List it, classify it, combine what you can, reverse engineer if you must, create a timeline.
In other words, define your mission, because the desired end point of the mission, guides the means and tangible  resources required to get there, and get it done. Then, marry up what you have as resources and expand them if you are able, and then learn or  devise the best methods to use what you have to accomplish your mission.
In less words as a mentor told me: “Run and gun with what you brung.”  (82nd Airborne, sniper, SERE instructor, deployed twice, so I trust him.)
2. If you haven’t noticed, training and gear cost money. If you have the skill make what you can make. One mentor was unbelievably handy at personalizing gear for both efficiency and comfort which is important for anything longer than a couple of hours, and that may be pushing it! And every skill YOU develop increases your survivability and utility to your group by some positive percentage.
But who do you listen to?
Remember point 1? If you have defined your goals – even partially or imperfectly – it will make your decision making process even in this area MUCH better.
Two key areas for example, are tactical training and outdoor survival. If you live in Texas but train outdoor survival in New Jersey only some of what you learn will apply. Broad basics will, but every environment has nuances as to where to get water, what to use for cordage, dangers, and of course differing climates which dictate exact shelter need and what’s available to construct it. If you can’t get local training, get what you can but get into the woods and make your mistakes!
3. As for tactical, if I had known what I know now..(the money and time I could have saved). However, he basic dictate is ‘don’t confuse square range training for tactics, and no pressure situations for pressure.’  Having said that, you have to start somewhere.  Basics with weapons are basics, e.g. safety, grip, etc. One level up is to add movement. Another is to add a timer, and still another to add physical exertion prior to shooting.  Every time a new level is added, it is amazing how accuracy, stance, etc,. go to hell – for awhile. Yet another mentor (SEAL) helped take some internal pressure off by giving me the training maxim: “Try, fail, correct, fail at a higher level.”  Basically it doesn’t give you an excuse to fail – the assumption is you will put forth honest mental and physical effort to succeed. But what it does do, is mitigate perfectionism before ‘perfect’ is remotely possible, it also builds in a certain ‘eagerness’ to fail in training situations, because while you don’t like to fail you see it as a necessary and useful pathway to improvement.
Moving up yet again, if you train as a member of a small team (2 or more) that’s yet another level requiring much more awareness and communication. And team mates get mad at each other from time to time.
As for trainers (and this is related to the point above), if they have a real background in instructional methods, listen to them. But you get a special and different ‘feel’ from instructors who have actually used what they have taught under real-world, stressful conditions. Not all trainers are fighters but can teach certain aspects very well, but if you have an instructor who has actually ‘done the business’ he can provide ‘informal’ knowledge – and wisdom – no one else could possibly provide.
They are also pretty good a recommending fine-tuning adjustments to gear.
Some will teach in a very straightforward way, and others are more indirect. Some set out procedures and drills, others  – usually after you master the basics – set up situations with no set answer, which becomes a learning and exploratory ‘journey’ of your own. In other words, you may have to carry a heavy load with a buddy  and it’s awkward, hard, and painful. You suffer. Later the instructor passes on ‘the trick’ and all of al sudden it’s half the effort on the next iteration.
That is ‘instruction by guided challenge’ which is one method that gets a real emotional learning component into play, and those seem to be the ones that really stick, because they were unpleasant to the body, and the ego.
4. Bottom line is ‘pressure.’ or ‘field test’ if you prefer. Whomever you listen to or train with there needs to be a progression to performance under pressure. Some instructors are quite conservative and build little by little, some it’s ‘trial by fire.’ But without unlimited time and budget you will have to take what your resources allow, but even so, ‘you need stress in order to progress.’ And a parallel for your gear. Crawl, run, scrape it up to see how to position it, and what gear is crap and falls apart. Especially check stitching, because much low end gear is hit or miss. It can unravel within the first hour of use. Basically, check fit and function. Does it ride well and can you reach what you need to reach from different body positions? And as mentioned, does it stay together.
5. You have to start somewhere. 
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