It's a start to acknowledge I have never walked in the shoes of a homeless person - I wasn't raised by my abusive uncle on the Pine Ridge reservation, I've never been a war vet suffering from PTSD, and I don't understand what its like to have down syndrome or schizophrenia. 

I would try to house hack if I were in your shoes.

Go into the property with a flat rubber soled shoe and scrape your foot across the floor like you're trying to dig a hole in the floor with your foot.

To me, one is an act of kindness, the other would be funding what equates to a gambling addiction.I'm glad I'm not in your shoes. 

What would you do in our shoes?

If I was in your lucky shoes, I'd invest the money in ADUs and JDUs on your existing properties. 

I was in your shoes once, and ended up helping my friend manage her 4 bedroom house that we were living in as roommates after she moved to out.

I'd just suggest you take a deep breath and first imagine that you were in your tenant's shoes. 

In the case I mentioned above, there were special circumstances of the sort @Rion Redinger mentioned.If I were in the tenant's shoes, I would feel deeply insulted if I got a "gift" from my landlord.

I like to put myself in my potential renters shoes and once lived near a busy street and it would keep me up some nights...let alone a big freeway!