I read this as someone using a short-term lens to focus on a long-term issue. 

Using your example, you sell Mon for your $155K and have a contract on a new home for $100K two weeks after this one sold.

Do any property managers out there employ (sub contract) assistants to manage the overflow of their responsibilities

Negotiating favorable terms is both an art and a science, and in real estate, it's a critical skill that can make or break a deal.

We like doing the hard work of doing due diligence, researching property histories, getting estimates, negotiating contracts, etc.We're also going to be looking to buy and hold in the near future possibly by BRRRRing.

Are you under contract? 

Thanks in advance,Keyshawn Good morning, the Destin market allows for short term, mid term and long term rentals depending on the area.

I own a property management company and also a contracting company in Ventura.   

Are you actually building the ADU or contracting out? 

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.