What actually are those issues, is it a software problem?

If it is worth fighting get a good attorney.Your By-Laws may allow you to call for an independent audit at the HOA's expense. 

I’m curious because I’m tired of collecting rent in cash, face to face... i also don’t want to pay a property manager  There are dozens of property management software that are cheap that allow online payments via ACH, credit card, and others. 

Anyone found software or an online tool that can do this?

There is free landlord software out there that will provide you with online applications and screenings as well as market syndication so your property is posted to all of the major listing sites. 

Hi all,we are Gianluca and Matteo, both Software Engineers working for major Silicon Valley software companies and aspiring real estate entrepreneurs.We’re currently working on a corporate housing platform with the objective of creating an automated service for renting out and managing corporate-level properties.

Where it gets fuzzy is - how much does HUD (their software, to be exact) expects to get, for the bid to be accepted?

I had a contract and brought an accountant in to audit the books for my account because the expenses for repairs and turns were so high. 

I'm a mid 20's software engineer by day, a platoon leader in the Army on the weekends (guard), and a FI/RE/investment enthusiast 24/7 (yes, I often dream about investments)!

Chris Goff has some software that looks great as well REIPro.