its doable:
I pretty much keep him up to speed on bike parts, but its a fine line when it comes to being supportive, giving him his space, not over bearing, and of course the worse thing I could probably do would be to simply give him everything.
we both have 56cm CAAD10s, I have a slew of wheels, tyres, etc... ad nauseam, so I simply keep a stash for him when the time comes. we both have each other bank acct #s, so when he burns up a set of tyres, I'll sell him a set. typically Rubino Pro's in 25c. I'll ask $40 for the set including shipping. that $40 bucks of course I just stash back in my "brother acct"
another thing I've been trying to encourage him with, is to know bike parts, and learn the art of scavenging, re-sale, and high quality mechanic services. I've had him help out with a few things here and there, like a big event, passing out leaflets, etc... and to show him what a quality wrench service is, how to interact with the guys, and what kind of money you could expect from something like handing out nutrition thru a car window.
I firmly believe in The Way of the Bicycle. simply thru default of efficient use of energy and now days the need to get exercise, as Huxley would refer to as "the reducing valve", which all processes pass thru... if one were fortunate enough to have the character to abide a bicycle lifestyle, that alone... for the most part, liberates us from most entrapments.
in regards to environ:
I often like to say something like "consequence is stronger than will", or the likes of "product of your environment". I was about 10 when I realized this on a schwinn varsity. if you are fortunate enough, maybe you can choose your environment. some can change their environments to lesser or greater degrees. I doubt that I could ever be a Thai monk, but maybe... doubtful tho. but I can choose to ride my bike to a different town, change jobs, and be mindful to what behaviors I engage.
thats the type of little quips I'd show my brother. small steps, choose doable goals, with long term objectives. bcz every day takes effort, and regardless you will make some sort of effort every day. if you choose to get up in the morning smoke a cigarette and complain about the govt, and lack of jobs, well... guess what... "thoughts in mind, produce in kind". chances are, you'll smoke another cigarette, and reinforce the idea that yes... there are no jobs out there. a year will go by, and you'll have smoked 360 packs of cigarettes, spent about $2k in the process, and have further isolated yourself from getting a job. Add smoking pot... game over.
wake up in the morning, get on bike, go for a ride, learn to fix something, be productive, even if its pumping a bicycle tyre. that is a skill set. there is a good chance that if you become expert tyre repair, you may get a job doing such.
so yes, it is doable, its miserly, and not too difficult.