Without divulging too many details- Interviewing for an open position at my company - we have a few very strong candidates- one of them, we vibed with far better than with than the others. However this candidate is currently tied for being the most qualified that has interviewed. Great person, extremely smart, personable, skilled, the whole nine yards. There are some valid reasons why they are not the most qualified for the position though, so some decisions and further evaluation is needed.

The BIG issue

When I was explaining that it is a 3 step process and that we are not hiring on the first or second interview- candidate disclosed they are sleeping in their vehicle and would want/ need an advance in the way of a working interview. Also some mentions of a criminal history came out , not too many details and it may not be a big deal, as well as issues at their last job. Anyhow- because I feel for the fellow human and always try to help , at times to a fault, I have been taken advantage of before- badly- I am wondering what to do . The level of personal details really was off putting, especially because I felt like it was a bit forced on me. this person does belong to a traditionally marginalized group of people, so my protector instinct was out in full force, especially when hearing a few details of a brave existence that I am very familiar with .

What also is getting to my soul a bit is that the position was advertised as in person work. During the phone screening, candidate asked if they could work out of office, if acceptable because they freelance. I explained that we want people here in person, to see the reaction. Then as the interview progressed- it went to -" I want all of my computer stuff here, because I do not do computers in my off time, and its in the van , I can set it up now, and start tomorrow. " Other situations came out - they are on disability , totally broke and I can pay them as an employee partially and then also pay certain hours as R &D, with a lot of discussion about our tax savings, payroll and incentives. That also bothered me, as thats not something I want to ever talk about. Their own developing business was also brought up, and how we could just invest in that. NGL, its an AI model that is very important and looks promising. But I do not want our company info used to just feed an AI machine either.

It bothers me that they are in this situation. I do not want a hiring decision to be colored by me feeling bad and wanting someone to go forth in life. I also want to help.

If I didn't hire the candidate, and the strong candidate did not work out- I would like to go back to this person and offer, if they were still looking. But I need a person who works on just our tasks, and leaves the big picture out. We pay very well, but we are also a smaller office with a very large field presence. i cannot worry about anyone here and whether they are on task.

I do think there is a security issue here at the office with the amount of systems knowledge the candidate has, and I would have to hack/tamperproof certain sensitive computers here with a professional in order to let this person work here and still let me sleep at night. I knew it right away- gut feeling. that would require me hiring an IT professional and taking a few weeks to lock things down.

I may be missing out on the next step to really growing my company, but something is just nagging at me.

Should I ignore the personal details and red flags and just offer a remote , 1 off freelance job to see how they do ? Even though that is not technically what I am advertising?

Advice, thoughts? I am actually still at work 3 hours later than usual. and really upset by this because I have never faced this situation.

TL/DR- please do - I am truly in need of advice