The primary reason I am looking into this option now, is to prepare for future scaling as well as prevent items from falling through the cracks.

You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year, not just when preparing your tax return.You want an accountant who can help you strategize and who is responsive when you want to know the tax consequences of the financial decisions you are making throughout the year.Good luck.

I need to prepare for this project by getting informed. 

As always, if you hire a cheap bid, be prepared to supervise.

It's not that you can't wholesale a contract involving an owner in default, but as @Jonathan Greene pointed out, you better be prepared to close.

I have experience raising capital for down payments if you are prepared to pay investors at this level.

I commend their effort for getting up and taking action, but many don't do the necessary homework and instead rely on YouTube gurus.Occasionally, you can find great deals from a wholesaler, but be prepared to spend a lot of time sifting through subpar offers to uncover the gems.

I have personally been raked over the coals on some south side properties with squatters because I wasn't prepared for the time it would take to stabalize the building.

Deegan and @Arda Bircan There are technically 7 Tests for Material Participation (but 3 that are most common) -> the individual 500 hour mark, that the activity of the individual is substantially all, and that the individual participates more than 100 hours + no-one else spends more time than them.Litmus Test: Are your hours integral to the operationsThe hours that qualify must be substantially all hours and have a legitimate impact on the rental activities.Activities that generally count: showing the property for rent, taking tenant applications & screening tenants, preparing & negotiating leases, cleaning & preparing the units for rent, repairs, and improvements, managing the construction, purchasing supplies & materials, inspecting the property, responding to tenant complaints & inquiries, collecting & depositing rents, evicting tenants, writing & placing advertisements, and working on your websiteActivities that don't count: education & research, investor-type activities, and travel time..

And pray they don’t steal everything one the way out. 4) Be aware you probably can never kick them out if they keep paying (at least not without 3-6 months of cash relocation fees.) so be prepared for this to be a rental until they decide to move out, not you decide to stop doing it. 5) PLEASE sell.