A trade would probably be better. "IT" sounds good. Air conditioning, office, etc but if you look at the jobs out there, a good portion of it is phone support shit masquerading as IT where they time your bathroom breaks and such. Also, a lot of the "dev" jobs are overcrowded and change people like an incontinent nursing home patient on fluid pills change diapers. Now, you can say those people suck or maybe were unlucky. But you do you.

I am assuming you are out of the shelter. I have been homeless myself. If not, Shelters fucking suck. Horrible people both clients and staff, strict ass curfews that hinder job hunts, etc. If you are still there, I'd forgo the drama with women (or just get a prostitute) and concentrate on getting better housing if not a dorm or the waitlist for graduate housing. Monk Mode is my suggestion if you are in that situation. While it is possible to get some trust fund baby girl with an off campus apartment that would solve housing to get around this, it's really too much drama.

As far as everything else, it's a numbers game. But, I would not limit myself to just college girls. There are working girls in that age range too out in the community.

Try online dating stuff. At least online, people are supposed to be there because they are looking. Which can be harder to tell in person. Talk to several girls and don't fear rejection. Be really cool and interesting (like you are). After all, if you can survive homelessness to go back to school, you have more epic badassedry than most of those punks out there.

Women are most attracted to older guys like 3-7 years older. So that puts you in the range of girls 18-22. If you want a skill that pays become a farmer, truck driver, tradesman, etc. I've been looking at jobs I'm qualified for(grower) and all of them pay over $100k. My 11 years in IT will most likely land me a tech support job at $30k. My Physics degree will most likely land me a teaching job at $30k.

You're young enough that you could go into the military and learn a trade for free while getting paid and getting free rent and food. Air force has the best bases. After 4 years you could go to college for free, get a low interest home loan, and serve in the national guard so you get a retirement at age 45. Take your trade and build your own business and be rich. When you hit your peak at age 35 you'll be drowning in college girl pussy.

Conversation is in the moment, we can't tell you what to say but you need to understand a few basics.

a) don't be afraid to argue with her, in fact teasing her about things is the best way to flirt: https://www.forums.red/p/TheRedPill/4972/humansockpuppet_s_guide_to_teasing_bitches/653684

b) become a more interesting person, learn more languages, read more, learn about art, music, popular culture, diversify your hobbies. You should be doing this ANYWAY to become a more complete person. Be a true renaissance man and you'll never be bored or boring in a conversation

c) If you find something good to tease she will respond positively and you can bring it up as an inside joke afterwards

d) It's less what you say but HOW you say it. At least 90% of conversation is down to body language, tone of voice, etc. Think about stand up comedy, you can say the same lines but if you fuck up the timing you lose. That's conversation right there.

Now, you don't hit up every girl on campus and say "can we go on a date", the approach here is slightly different. You need to be a very sociable guy, you talk to EVERYONE, men, women, lecturers, whatever. With women you find attractive you flirt, and when they give you IOIs and flirt back, that's when you know you can ask them out. This way you're practically guaranteed a date, you expand your social circle so you have a lot of avenues to meet new women AND you get some nice social proof, and you're not that creepy guy that got rejected by 30 women last week.

Cold approaching and asking for a date or number within 5 minutes is something you do in a gigantic city like london or new york, where you'll NEVER see her again nor any of her friends. You don't do that on a college campus where all the popular kids know eachother, does that make sense?

Also 25 isn't old, you're actually in a better position if you're slightly older because women don't date guys their age when they are young. There's a nice chart online about what age they prefer but it's always slightly older until about 40s and then they try to go for younger guys but fail and quickly correct. It's pretty funny actually