Just curious... what’s your ultimate goal for that office space..are you looking to boost resale value, or is it more about having a functional retreat above the garage?

But ultimately, with the property now stabilized, we feel like we should see solid rent and price appreciation over the next 3-5 years.

After a bit more research, I actually think renting a place will get me started faster and earn some experience doing Airbnb with a little less risk involved.Obviously I still need to be concerned about not violating a lease agreement by doing so and I would likely live on the property and lot or all the time.Ownership is still the ultimate goal, but this looks a faster party to self driven income.

LLC's separate your personal assets from your investments and offer you protection from lawsuits related to your property, they can help to establish a more professional image if you plan to expand, and they provide some flexibility on how you are taxed.There are some drawbacks, included fees and administrative work, but it's ultimately best to consider speaking with a CPA to determine the best option for you. 

Ultimately, it’s about finding an arrangement that aligns with your goals without compromising your ability to discover the best deals.

And for example there was a Crowd Street deal (Nightingle) where the sponsor omitted losses from their claimed track record (and ultimately was fraud...they never even bought the claimed property).And there appeared to be some difficulty or confusion with obtaining the full and complete track record ( including both realized and unrealized deals).

Of course, if the ultimate plan is to run it as an STR, then it has to be analyzed through that lens. 

The issue we had is that over time, our sheets get mixed up with other customers' (cheaper) sheets, and we ultimately end up with an inventory of sheets that are not ours.

Ultimately buying real estate without down payment funds is far trickier of a process.

For more info on Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods.