The goal is to mitigate the risk as much as possible with finding a good location and solid property.

This approach would allow me to learn with each deal and minimize initial risks.2️⃣ Go Straight to Multifamily: Instead of starting with SFHs, I could spend time learning the multifamily business and go directly for a 20+ unit building, maximizing scalability from the start.I have no experience with either strategy.If you were in my position, which strategy would you choose and why?

This establishes the legitimacy of the arrangement and protects against audit risks.

Starting with a single-family can be a great way to start especially if you’re looking for a lower-risk starter project where you can get your hands dirty and learn a ton by doing.

You don't want to risk killing the goose that lays the golden eggs.

If one of the greatest investors of all time believes stocks are overvalued, this may be an opportune time to shed some risk and move into a more tangible asset like real estate.The Rochester housing market is a great place to consider for investment.

If you decide to take the partnership from a trial, to an ongoing long-term partnership, then get the attorneys involved and create an ironclad, partnership. 

Low risk property. 

This is not worth the effort and risk of owning a duplex.

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.