I've already read a few books and been sitting in a few pod cast but none seem to answer my question.

I just don’t want to take the chance of it messing up and having to sit with those major costs.

How long would you let a tower sit empty before you tested the condo conversion model?

Hopefully you have this provision in your lease.Unfortunately if they are the other kind of uncooperative(constantly late, major lease violations, or filthy beyond belief), you probably are best letting it sit vacant.

It looks like as property managers we will have to sit back and wait to be contacted.

By 3-6 months they realize they are sitting in the same property they wanted to get rid of and might be open to off-market (no realtor, they blame everything on them) deals.

I then asked, what if someone had a property sitting vacant because it couldn't be rehabbed due to covid"...the guy I spoke with didn't seem too sure how to answer.Anyway, to be safe, I'm just going to call them anytime I'm unsure of an expense and then document (day, time, agent's name) for my records just to be safe.

@Anthony Gayden yes, if I plan to go forward I am definitely going to sit down with a fidelity advisor to go over everything.

Key to getting funding or financing from any lender is having your homework done and being able to talk-the-talk before sitting down with them.   

You're much better off letting the property sit vacant a little longer while you wait for a good/qualified tenant, than to rush to fill your property with a bad/non-paying tenant.