If they work independently, set their schedule, and use their resources, they might qualify as a 1099 contractor, but misclassification risks IRS penalties.Wages for W-2 employees and payments to 1099 contractors are both deductible business expenses, but compliance is key.This post does not create a CPA-Client relationship.

I do currently rent out a condo, fully furnished on furnished finders, and that has gone smoothly.Any tips, advice, etc accepted! 

And if you're not already using the same paint color on all properties, you should start and you can thank me for this tip later.

Happy to be a resource as I know all of this is challenging.

@Josh LansberryWelcome to the community and be ready for a huge amount of information at your finger tips.

One more tip – people remember stories that trigger their emotions.

Quote from @Mitchell Gunlock: Quote from @Cliff Benner: Looking for Tips on how to find places that have multiple cabins or additional dwellings on a property that I could live on and run.

You can also use online resources such as City Data to search demographics in the area. 

Any tips on finding reliable professionals in my area?

The base is $17.20, plus tips.