Personally, I use pooled accounts: one for all rents and property expenses*, one for Security Deposits.

You can't charge extra pet rent or even a pet deposit because it's legally not considered a pet.

My partner and I keep an excel spreadsheet of rent, our purchases, utilities, taxes, insurance, and money spent on contractors.

I would definitely start off renting most units as LTR and slowly renovate and furnish units to do MTR, having a mix of both. 

location location location  Wow. 

With a 9-5 job too busy to catch a breather, being that it will be my first rental property would you recommend finding a property management company to oversee the investment property OR create a profile on a property management platform, I am thinking about Avail unless there is a better platform, to collect rent and hire specialist as issues arise from tenants?

These software's can run all kinds of reports and also help you with rent collection and accounting for vendors etc.

Biggest struggle is finding deals that make sense where the numbers work and in locations that would work for STR.

Let’s break it down.Self-Managing Your Chicago House HackPros of Self-Managing✅ More Cash Flow – Property managers typically charge 8-12% of monthly rent.

You would basically offer the same set up utilities but you would have a residual income monthly by renting the plot to the owners of the space.