But I feel as though it would get much more complex, and wouldn't I 100% need to get a PPM in that case? 

Most people just don't realize the complexity of the tax code / laws.

Respond to maintenance requests quickly.Maintain the property well.Treat residents with respect.Properly screen tenants in the same complex to create a community of like-minded residents.Respectfully enforce lease terms regarding on time rent so their is clarity and consistency among residents.Respond to items that impact the overall look of the exterior of the property (broken blinds, sheets or signs in windows, storage on front porches).Properly maintain landscaping in communities.Provide automation for applications, lease signing, renters insurance and lease payments.Deal aggressively with unlawful and non compliant residents to provide a safe community.Understand and price rents at market levels.If you are raising rents, offer to clean carpet (if needed) or add/replace a fixture...get creative to add value.  

Taxes in Cook county are complex and are going up.

Matt,Entities are inherently complex, and there's not one answer.  

You should also evaluate how much protection you actually gain from using an LLC given the additional complexities.  

You could do a partial conversion on a single property, but then tracking and allocating the value as well as share of expenses and income of tax-deferred vs Roth for that property becomes a bit complex.

This is sweet!  

They have a ton of modern features (digital leasing, online payments, online inspections, etc.) and they are constantly updating the system and adding new featuresI have also worked with Buildium as one of our apartment complexes uses Buildium.

@Mark Forest , I know that depreciation is a very complex area of tax.