Read some books. 

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

I've read BiggerPockets' Real Estate Investing book and am particularly interested in the house hacking strategy, as I'd like to move out of my current living situation.Our main dilemma is choosing between a single-family home (renting out one room to a close friend) or a multifamily property like a duplex or triplex.

As for the initial post, I would ask a few questions to shed some guiding light.

I’d love to help guide you through this!

@Dennis KnappJ Scotts book on estimating rehab costs is a great start. https://store.biggerpockets.com/products/the-book-on-estimat...Here is a "general" rule of thumb for my market in Jacksonville, FL.

Close to a cool little town, close to an area attraction, etc....Also do a search here and see how to screen guests, in addition to what the hosting sites do.... like no last minute bookings, no short stays....

As you look deeper into Cleveland, check out The Ultimate Guide to Grading Cleveland Neighborhoods.

That's the opportunity.I also recommend engaging an 'investment focused' realtor (not the general residential ones) to guide you through the process and provide you with market intelligence. 

We already have a few mid-term booking requests so just as I thought, my vision of what's possible is coming to reality.