While I’m new to the business, I’m eager to learn, grow, and connect with local investors, landlords, and fellow real estate professionals.

If you plan to expand your portfolio, forming an LLC can simplify liability protection and operations for multiple properties.Consult a CPA or legal professional to confirm your tax obligations and evaluate whether an LLC or umbrella insurance aligns best with your investment goals and risk tolerance.This post does not create a CPA-Client relationship.

Plus, professional management companies often have tools and strategies to maximize occupancy and revenue, which can offset their fees.

I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

I guess that you could call me a 'professional host'.  

Great tenant that always pays on time - been there for 5 years Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

Here is a newly created resource on BiggerPockets, which touches out cost segregation, accelerated depreciation, bonus depreciation, depreciation recapture, Real Estate Professional Status (REPS), STR Loophole / STR Strategy, example properties, and more. 

Any guidance or referrals to professionals you trust would be greatly appreciated!

This is platform for professionals and novice investors and you will learn a lot of valuable, hard-earned lessons in a short amount of time.