However, the floors were done around ten years ago and the precise flooring can’t be matched.I was wondering if I should trust the management’s repair crew to do a proper job or whether I should make specific requests, as this type of situation is new to me.There is a cooperative tenant residing in the condo.Advice would be greatly appreciated.

What are some realistic expense figures that I can plug into my proforma to evaluate this property assuming it's properly managed?

If they are not hard wired, you may have to pay an electrician anywhere from $2K - $6k to wire them properly. 

But I also want to ensure I'm not using unrealistic criteria.

I will ensure to reach out to her and see what options she can provide. 

I would like to utilize the HELOC to lend to the partnership, from my own LLC (which would be paid interest above what the HELOC charges) but am wondering what hurdles I need to jump through to do it properly.

It’s always a givers gain and we need to ensure that what we are giving is something of valueBest of luck to you!

I thought I had read somewhere that if you're month-to-month/holdover, the landlord can raise rent with no cap (at least the # of times) provided they give proper notice...unless that was the law *prior* to the bill being passed last year? 

By the sounds of it you are not seeking money, you gave proper 30 day notice the month to month would not be renewed past X date and you are now beyond X date and you want your property back. 

Additionally, I would post, call, and leave a message stating that you need to come inside the property to inspect with proper (our lease states 24 hours) notice.