I started with Podio (Premium) and already I am seeing it's limits without having to spend a lot of time customizing it or hiring someone to do it or even paying a monthly fee to some third party.

Especially if you are hiring property management.

Go through the formal eviction process, hire an eviction attorney.

One of the biggest challenges for everyone involved is being on the same page about the actual time required for maintenance.DIY landlords rarely properly track their time when it comes to property management in general - tracking their true time invested in maintenance is where they perform the worst.Investors that hire PMCs are rarely any better at understanding the true amount of time maintenance takes.

If HOA by laws state past due owners are responsible for all late fees and legal expenses for collection hire an attorney to go after the past due. 

Then hire a handyman to put everything together.Rooms to go sells whole rooms full of furniture, sometimes at zero interest.

In order to get there it would be good if you could keep feeding cashflow proceeds back into acquisitions, on top of your continued W2.Speaking from experience, you can manage probably 30-50 units yourself nights and weekends before you really need to hire someone.

At REI Nation, the owner can hire our management company. 

Also, for people who wish to pursue larger real estate ventures, you don't personally need to be able to analyze a deal, and can possibly partner with someone who does or even hire an underwriter.

You can also hire a real estate attorney off of UpWork or Fiverr to review the documents and give you an opinion just to be sure.