I am interested in buying a long-term turnkey property in a nice area (I live in San Diego so this property would have to be out of state).

Quote from @Nathan Gesner: There were a couple experienced investors on the forums that loved to tell everyone they could manage a short-term rental in just five minutes a week. 

What were some mishaps along the way in terms of the contract?

My name is Wes and I live about an hour north of Toronto, Ontario, Canada.Looking to get into real-estate investing with long term rentals, BRRR, and House hacking.Currently looking to also find other other local people to chat to about real-estate and how to get started in our currently price inflated Ontario market.Let me know if you're in my area!!

Then do a thorough research on tenant applicants (note: leaving this to a PM may be hazardous to your financial health) and choose the one that is most “stable” with the best potential for long term tenancy.This advice is contrary to maximization of rental income, but IMO will reduce expenses of tenant turnover, property damage, property management fees so much that the difference in bottom line income will be quite small.  

Raising money is all about marketing and sales (not real estate specific) so either hire marketing agency and read sales books, or hop on some LinkedIn courses on marketing and sales.Not sure the legal structure to use: talk to accountants and attorneys.Need deal flow: talk to brokers and go to a lot of networking events.Lending terms: start calling banks and loan brokers.From there, it is all risk mitigation. 

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With countless loan options, complex terms, and strict lending criteria, it’s easy to feel overwhelmed.

I think 1) 10 years that includes recovery from GFC and the Covid pandemic is not a long enough duration2) I think for those 10 years, 100% is not that special3) I think many Midwest markets did not experience the appreciation you depict.There are Midwest markets that have pretty good long term appreciation but there are also many Midwest markets that have appreciation that has not historically kept up with inflation.  

It really is a minefield out there.I know everyone likes the convenience of the web, and they are tired of hearing it, but this really is a business based on relationships, not online anonymity.