That said, I can handle it when necessary and have successfully built multiple self-started businesses and ventures in real estate investing (REI).

As an investor in a couple of Jorge Newberry’s note funds, I came across one of his newer ventures: preREO.

who are involved in wholesaling or other real estate ventures.

Here is a solid example you can adapt for a joint venture (there are differences, beyond just nomenclature, for a partnership and a joint venture): https://templatelab.com/joint-venture-agreement/Again, I would caution use of this document without a professional to review it.

When one machine goes down you start losing money in a small way. 

Just try to sell it to someone else for anything so you don't lose all of your money.

There are other downsides that need to be added to this list, both related to resident psychology.When a resident has a security deposit, they consider that to be their cash and they don't want to lose it. 

A little over 15 years ago, in the late spring of 2009, I was a brand spanking new real estate agent coming off of a miserably failed real estate investment venture.

:) as for now, my next investment venture is Short Term Rentals.

Stay in and be part of this 721 or lose my investment most likely.