Also, Ive bought office supplies, went out to eat with contractors, and more, should I be using a business credit card? 

It's a business so the rents will be the main income and subtract expenses including savings.  

I am one to give people benefit of the doubt but it usually ends up with hurt feelings and regrets in business.

I currently am a realtor in Illinois and I operate my business under a LLC.

SOFTWARES/TOOLS WE USE:Quickbooks (just changed from Stesa) - AccountingGmail / Google Drive - I create an email for the business and use this as a shared drive for all of my rental documentation.

I just started experimenting with Downtown Detroit with ATTOM's "sales snapshots" and I haven't gotten that kind of performance yet.

The old saying "Focus on the business and don't be in the business".Find a trustworthy PM (Easier said than done) and let them manage for you."

Or even STR is also a business. 

No offense, but you want to act like a company or business to make money, but you don't want to take responsibility like a company or business.

I've been told by my attorney (i'm a private money lending business owner) that we do not accept payments post maturity unless we do a new written extension or loan modification with agreeable terms.