All landlords experience situations like this (experience through pain/expense). 

It was a pain in the neck and one of the many reasons I decided to drop my listings from VRBO. 

We also bought at high interest rates, which was painful, but the kicker was insurance costs near the coast.Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I used to print it as well but that can be a pain if and when anything changes.  

you are kind of dealing with three diffrent issues here, the thing about not being a legal three unit, super easy don't buy something that's not legal, and your agent really shouldn't be encouring you to break the law, the issues with properties being beat up, the vast majority of multi unit's that sell have some wear & tear that's often the reason for selling, being a tired landlord, if you want turn key, you are proably looking more single family homes or paying big dollars for a turn key multi if it even exists in your market, 3rd we can debate the pro's or con's of this this market but youve hired and agent and 99% of agents are going to tell you its a great time to buy, i'm usually more measured but that's because I have a deep psychological problem in which I care more about being intellectually honest than making money, most agent's however are not afflicted with this disease so your gonna have to make this decision for yourself before you hire any agent.

Long-story short, we don’t “need” the clients, and the clients don’t “need” us, but we have found there is a strong value provided to clients who do decide to work with us and want to avoid a lot of those early on trial and error pains and expenses.

If you can take a little financial pain, I think it is better to list in the slow season.  

  $500k net would have me considering selling, but it sure would be a pain.

Having said that, my spouse and me work in high stress jobs and having some level of constant income coming from RE investments would be good psychologically if we want to take a break or lose our jobs.

The platform must align with  investors' specific needs and preferences.Ultimately, the mission is to flip the script on prop tech and deliver a game-changing solution that tackles the pain points investors face head-on, empowering investors to reach their investment goals with confidence and ease.But here's the thing—we can't do it without investor participation.