When I spoke with a real estate professional, she said the home would probably sell for around $250k in its current condition.

However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

My goals are to start building an investment portfolio of professionally managed (I could tell you all the reasons I will not do it myself) multi-family properties and, in time, develop a property in the Northwoods (Wisconsin/UP).

It has cost many people including myself a lot of unnecessary money and still is because you deal with the tax portion of opening unnecessary LLCs recommended by supposed professionals. 

If you know of any exceptional professionals in the Cleveland area with a strong track record or if you believe you are one yourself please reach out to me and I will get back to you.

It sounds like the reason you wanted to do this was to achieve Real Estate Professional Status. 

If you have limited prior experience owning / operating multifamily assets, they'll also require you to use a professional property manager with multifamily experience.

In the world of accounting, different levels of education, expertise, and responsibilities define a professional’s title and role.

Ask lots of questions and you will receive great insight from professionals!

I’d recommend starting by connecting with local investor groups and networking with other professionals in the area.Also, seek out teams that are actively investing and managing properties on the ground.