Then I can screen accordingly and either have them sign longer term or terminate their residency.

(make sure your contract specifies that you get deposits and pro-rated rent when you purchase)Only thing you can consider requesting is that the tenants be put onto a new month to month lease. the benefit to this, is oral leases can only convey rent amount. this lease is created by accepting rent from the tenant every month. every other stipulation defaults to state law. this means tenant can show up tomorrow with 3 pets and you cannot do anything about it (except provide notice of lease termination) whatever you do keep the current tenants on month to month.

You have clearly seen the benefits of holding property long term in this area.

Fast forward to today and we list the home, get it under contract in 5 days, and then the buyers terminate the contract because the foundation.

We couldn’t, they didn’t, and deal terminated 1 day before anticipated closing.

I found an apt right away and asked her if she would agree to an early termination of 30 days.

It's such a rock solid neighborhood -  16 min Metra/30min Blue line to downtown, 94 and 90 access, bus terminal, and a disproportional amount of city workers with good incomes and families.    

If the PM refused to agree to this, I would tell them they will be terminated and take them to court for the money.

Terminate the purchase agreement.Option 1 doesn't cost the Seller anything.

I would serve her a notice of lease termination/non-renewal, and if she leaves on 9/30 then deduct any late fees or rent shortfalls from her deposit (although I would still be trying to collect it from her all the while).