If so, I am having trouble deciding on whether to create an LLC in Maryland (where the properties are) or Wyoming (cause of the know benefits).

There are pros and cons and it's important to be aware of the drawbacks as well as the benefits. 

Also, read the contract very well before you sign because most PMs will lock you in a long-term contract.If this is your first investment, I will recommend you manage it yourself so you learn one or two things about landlording/property management.Goodluck man!

I was approached by people who are interested in leasing my property long term and use it for cooperate business travel accommodation. 

What recommendations do you have in terms of what to take a look at/action items after 1 year? 

Especially with a long-term hold approach.

My latest and nicest building is in the bottom 2 towns in my area in terms of services and overall location.

The short-term view is you lose money. 

They should be able to guide you through the benefits of each scenario... just tell them you're thinking about living in the quad or potentially just renting out all four units.

First unit lease is up for renewal on 10/31/2024 and has a good long term tenant.