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. 

Put yourself in his shoes, and now he's got these "kids" coming along worrying about 0.5% and opting into higher minimum monthly payments to get it.

What would you do in our shoes?

I would call them and just let them know (nicely) that maybe shoes off is a good policy etc etc. 

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! 

Your options are to bite the bullet and do the renovations to get applicants who can, at least, tie their own shoes.