Quote from @Virginia VanOeveren: To start as a private money lender, educate yourself on real estate investing and lending practices, define clear loan criteria, and conduct thorough due diligence on borrowers and properties.

Practice your pitch!

I love how you reframed failure as a stepping stone to success.

Not sure if this has worked through but a winery that has been long on the market might be suffering from poor practices by the viticulturalist.

What is the next step for me as a new landlord/homeowner? 

Without reserves, they might be unable to evict tenants or prepare the units once they are vacant.Great points—walking the property and speaking with tenants during due diligence is a practice we now prioritize, along with running tenant histories through eviction databases.

Ideally you'd be there too (or a manager if you had one) as that is best practice in my opinion, but being remote you just have to outsource everything to people you trust. 

If it escalates, they can step in and mediate if needed.

Unfortunately it's not practical in a rental unit.

For me, it's about practicing Cooperative Group Economics: It's not about me maximizing my profit, by rather about me maximizing the benefit to my community.