That said, here is how I would proceed...For some background, I used to run an STR management company in SATX and we peaked at about 35 properties under management. 

If the negative cash flow is manageable and the appreciation potential is strong, it could be a smart move.On the other hand, investing out of state allows you to enter more affordable markets with strong, steady returns, helping you to build a diverse portfolio over time.

Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

With average rents in Charlotte hovering around $1,800 to $2,000, that means an average agent fee of just $190—if the management company even pays the showing fee.I understand that this may vary by market, but in mine, I don’t see agents being incentivized to work with renters.

If there’s a significant difference, it might justify the cost of adding more beds.For example, we manage a 4BD property where one bedroom is currently locked off, so it only sleeps 6 (1 king, 2 queen).

The other contributing factor was the poor property management and sponsor asset management of the properties.

@Brice Alef-Torrisi putting each property in its own LLC is usually overkill.Getting a bank account for each LLC is typically something you need to do to avoid "piercing of the LLC corporate veil" (actually depends on tax selection you made for LLC), but is also overkill.You haven't indicated how you are holding the deed for the latest property.If in your name or same LLC, you don't need a separate bank account.If in separate LLC, you can create a Master LLC, have each property LLC hire the Master LLC to manage their affairs, and just get a bank account for Master LLC.This is an opinion, not advice, so lookup CPA Frank Alcini in Troy for expert advice.

Quote from @LaShon Evans: I manage 400 rentals and own 33.

I'm a managing partner at a holding company that does things a little differently, and we have a one stop shop for everything.

Consider reaching out to a local Rental Owners Association to connect with experienced hosts, gain valuable insights, and access resources that can help you navigate property management more effectively.