If possible, in the future I would try to obtain a copy of a standard Condo questionnaire from the HOA prior to the mortgage application process and ask your lender to review it in advance in order to mitigate some of the time and costs risks associated.

I would first check city/county STR rules and HOA (if applicable). 

.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

Worst case scenario, if that doesn't work, I can simply do fertilizer applications and landscape lighting as they don't require much labor.

Unless you supply the 3M ones I guarantee the tenants are going to use the Dollar Store ones that leave torn paper everywhere. 

However, without significant updates, they’re likely to reject your application outright without leniency. 

My issue is, it's been almost 3 months and I haven't be able to get good tenant applicants.

Challenge is where is their motivation to properly screen applicants and get rid of nonpayers?

The window for application won't open until what's now a draft proposal becomes law.