I’ve tried to do a retreat of A-frames in the mountains but ran into land/engineering issues, multiple times. 

Some states like california you can do trust deeds where you break off the loan into multiple pieces.All of these will require significant capital to scale with your own funds. 

Quote from @Sunil Kale:I have multiple grounds for eviction (many late payments, many HOA violations etc.)Please get some education on how to manage a property or hire a property manager.  

I have a do use multiple tools for PM management.

The more time you spend on administrative tasks coordinating with multiple service providers, the less time you get to spend on managing your properties, finding new potential investments and increasing your financial returns.Tax strategies and property insurance are two areas that are highly customizable because no two portfolios are identical.

I have seen it multiple times. 

Do you want to get into what can be a years long battle with multiple parties, including our darling city council, until you get to move into your home the way you want it?

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

January rolled around and we suddenly had multiple offers.

You won't have multiple systems--one for CRM, one for PM, another for collaboration.