You sound like you have a good grip on this and are proceeding with an appropriate mix of passion and reason. I am not much of a financial success personally, just an average earner but I found a happy balance between paying bills and feeding my passion to fly. In my case it was a mix of office life and flying. Most pilots will tell you having rods in multiple fires is the only way to pursue an aviation career because of the inherent instability in aviation. So even if you decide to be a real live pilot one day, you are never going to want to relinquish those side gigs. So, my advice is to do all of it. Try to develop the web development business, keep your day job for now, and be as vigorous as possible gathering flight ratings. Do not take out loans for any of them. I repeat, do not take out any loans for them. Doing all this is a tall order but it can be done. Your flying will probably always be a net loser in terms of finances, but not doing what you love is sort of like not living. Good luck, you have a lot to do and many enriching experiences to gain.