So running things on a day to day and month to month basis becomes much easier as operations get bigger and more complicated.

This is a more complicated question.

We were okay with paying a bit extra for something we love, but with the added complications of the undisclosed claim and the high insurance premium due to the property being in a high-risk status, it’s become a concerning situation.

Underestimating the time commitment necessary for successFunny how the more complicated, higher risk, and more knowledge required to succeed in a Particular aspect of real estate the easier and simpler the gurus make it sound.

Some stories are too complicated to explain just on a forum but happy to share if you would like in a DM. 

Investors are advised to consider more traditional real estate investments and to educate themselves thoroughly before diving into the STR market.It is actually way way more complicated to have STR in Lake Tahoe rather than in Hawaii ….

And there is no function at all to import transactions from my property management companies, so I need to keep a separate set of books for things I pay and then have my accountant manually reconcile my books with the property management statements at tax time.Fourth, it's incredibly complicated and hard to learn, but the customer support is very limited and rarely helpful.

This gets complicated with two sets of participation rules for limited partners and individual taxpayers.

@Spencer Speckles,  there are additional complications if you try to carry back a note while performing a 1031 exchange. 

I'm not sure most brokers would allow people to do both, but not sure about that.Personally I have more than enough to do on the real estate side, I don't need to complicate it any more by adding mortgage.