Rental Procedures - Potential Acquisition - First Property

[Nicholas Call]

My family has a rental property in a Class C neighborhood near me and I was thinking of working out a succession plan with them. Before jumping right in and discussing the logistics with the family I'm trying to find a solid game plan and strategically implement some processes that may make property management more passive / manageable for me as I am working a full time job. I want to network with a local repairman and potentially get them setup on some sort of CRM / work order system. My goal is to not hire a full time management company. My background is in accounting / finance and I have managerial experience in business. First building is 3 units and the second I may want to acquire in another year is 4 units. Buildings are side by side.

Is there a software or any advice one may have to get tenants converting to depositing rent directly into a bank account to try and automate the rent collection process? Create an account with the bank in town that's within walking distance maybe? I'd like to avoid CC rent collection to avoid potential charge-backs. Currently tenants are accustomed to having the rent picked up and it has created some inconsistency on rent collections. 

In addition to rent collection I am curious of a software where tenants can submit a work order and I am able to assign this to someone for repairs (designated handyman). I want to reduce late night phone calls unless it's a complete emergency, smell of gas - burst pipe etc. 

Does anyone have a recommendation on an affordable all in one system that can handle A/R - Work Orders and accounting functions (ideally p&l performance on separate properties as the portfolio expands). In addition any advice on instilling the preferred behavior into long term tenants to try and get everyone on the same page?

Any other advice once the acquisition may take place as an incoming landlord with the change of guard within the same family?

Thanks in advance.

- Nick