Because I can spend 40k on a paint job (if I wanted to) and no lender would cover that expense under delayed financing exception loan on top of my purchase price.

My thoughts are I was planning on doing the upgrades once he moved out anyway, and if I could get him to cover some of the cost, it may be worth doing now. 

I agree with @James Wise that you must cover all of your bases when investing in a property that you cannot physically see.

I’m pretty sure we can’t promote here on the forums.

I think you're right, they may see it going toward foreclosure and the ridiculous time and expense in NY is not worth it and may not even be covered by the equity.

Lisa BoyceChase GambleKrista WilsonBetween these three you shouldn't have a problem getting ALL of your bases covered... 

But in those cases you are increasing rents to cover increased expenses and maybe padding a bit to your advantage.The downsides to both are that when tenants don't pay for utilities, they tend to abuse them.

What creative income generating thing could you add on the property, to cover for the extra payment? 

@Raymond Kovats, either way, my question is: will renting it out cover all its ongoing costs (including the HELOC/Refi loan)?

The refi must at least cover the original loan, and as much of the Rehab, holding costs, and closing costs as possible.