That allowed me to immerse myself in the Chicago real estate market/industry which has been an absolute game changer and dramatically changed my life's trajectory.  

You can boost your home's curb appeal by planting flowers, trimming shrubs, and removing leaves and debris.

I was wondering if anyone has been successful "upselling" rental income by offering extras to boost monthly rent.  

If I were you I would look for listings that are underperforming where you can come in and make some easy changes that will dramatically increase their booking. 

You can also sign up for Experian Boost which should more than offset any hard checks you get. 

When a hot water heater is over 10 years old or an HVAC is over 20 years old, the likelihood that it goes out increases dramatically.

STRs have the potential to boost values, yes, but that mostly raises their property taxes.

The money you save on rent will be a major financial boost and you will start reaping all the rewards of long term property ownership you mentioned such as appreciation, loan paydown through payments, tax deductions etc. 

Using a standardized email for every applicant, every time, will dramatically reduce your workload and end the confusion.

Right now everything from materials to labor costs are at their peak and they fall dramatically during a recession.