They hired our lawn care company to cut the lawn/shrubs.

As an investor, you cannot afford to hire a poor business operator.  

If I were to hire this out to a manager, would they actually be able to do a better job then me or would it be worse because they aren't as invested?

Once I was ready to go full time, I hired a mentor to set us up for success.  

Do you hire a real estate agent to rent it for you?

The property manager in place when we purchased, we thought we'd hire too until we read their owner's agreement.

That being said, they may not be doing it directly themselves, for example they may hire an agent who has access to some off-market listings as well as doing a general search on the MLS.

I like doing the lawn service myself because I’ll hire someone that will go by there the same day, each month or every other week and take care of it and it will always look nice and neat.

Hire separate contractors for each of the big jobs.

I'll actually need $275k to get the project done and the guy I had hired walked off the project during the beginning of COVID and basically isn't coming back because he's so busy with more lucrative business.At this point, I'm not sure if it's worth it to sell at a loss ($40k loss), or wait until lumber prices come back to 2018-2019 levels and just pay Property Tax on the land until then, or just spend the extra $100k to get the duplex built with a different builder and call it a day ....