. - $15k. in upfront costs for furnishings to linens, etc.

You'll want to have some anyway, to preserve the possibility of using it as an LTR and to store household goods, linens, etc. but things such as walk-in closets would be wasted in a STR.In-unit laundry facilities are another thing that aren't necessary.  

I don't think at this point I'm clever or brave enough to do more than one deal a year, and as time goes on we'll see if I pick up steam :)Thanks Cara, I really appreciate the response!

Examples of services that would be considered “substantial” are: Cleaning of the rental each day while the property is occupied by the same guests.Changing bed sheets and other linens each day while the property is occupied by the same guests.Concierge services.Conducting guest tours and outings.Providing meals and entertainment (like providing breakfast each morning).Providing transportation.Providing other “hotel-like” services.At the end of the day, the more you look like a hotel or “true” bed & breakfast, the better the chance that you will need to report your income from the rental on a Schedule C, and pay self-employment taxes on that income.If you don’t provide substantial services to your guests, then the income from your short-term rental can be reported as passive Schedule E income that is not subject to self-employment taxes (which is obviously an advantage).

She still messages me with linen suggestions etc.

I want to warn other investors to be mindful of such a charge and perhaps ask their realtor to be as thorough as possible to help ensure these charges are brought to light before the transaction ends; and 2.) see whether any other landlords have any clever ideas for possible courses of action we can take aside from what we've already done.  

Maybe clever questions they ask or things like that. 

@Jeff Richardson I like the idea of a library that is very clever!

I hired an attorney who specialized in real estate law in that town, and he said she was the most clever evictee he had come across.  

For listed properties, the L/A can input owner name manually in my area, so sometimes they'll put "Owner of Record" or "Client of XYZ Realty" to be clever, but I can export public records data from there instead of listing info.As others have indicated, you may have to search for an agent willing to share this data with you and disclose fully what your intentions are with it.