I am currently looking for an internship to gain practical experience in managing STRs.

So, we found a property manager through a friend and fell into the business.In 2023 we decided the real estate thing might work, refinanced our property from 2009 and bought an additional rental property in the same area placed it with our current property manager… on purpose this time.

Buy 4 more properties - one approximately every 3 months, based on the following logic = always fill existing property with a tenant prior to moving on (I'm new, and this is my way of managing risk); build resources to purchase next property (I have pretty decent purchasing power right now through conventional lending with my current job, and I also have a private lender ready to loan on my next property, and I also get a quarterly commission check that provides a nice financial bump every 3 months); finding a property takes time, but it is worth it to find the right property in the neighborhoods I want to invest in, at the right price.

Contractor management is one of the most challenging parts of the business.

I talk to our local Section 8 office frequently as a property manager and in the begin they made it VERY CLEAR that the minimums are to protect the landlord AND the tenant.Most likely, the tenants are not going to have excess cash flow or savings to cover any of the damage to your "upgrades". 

Did you not get bank statements or anything from them or the property manager?

It can be more challenging to manage your calendar to keep space for the longer MTR bookings, though.

Obviously I’m in Canada so would need a property management company so that would add to the expenses, but I don’t know, something feels right about an investment like this.

They are expect property managers in Atlanta and can help you navigate this chaos. https://www.pmigeorgia.com/about

Once you find your 1st property, hire a property manager.