The biggest challenge in furnishing it was getting the furniture there.

You can only get the depreciated value of the furniture. 

Has a gated small backyard, a shed, a concrete patio, and a walkway to a firepit.

They know you aren't trying to get a Target card and a Furniture card and a Macy's card to run them all up.

If you are adding some furnitures I would look into Facebook market, I have found a lot of great pieces for free or super cheap in almost new condition.Good luck!

Premium condo and a lot of high-end upgrades and furniture.

For example - you buy a property that needs renovations, upgrades, furniture and decor for a short term rental.

However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.Bills / property taxes are about $12,000 a year.The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,).

The grime just really adds up and if you don't stay on top of it it can ruin rugs, towels and furniture. 

Otherwise, i THINK the technical answer is to treat it like a business startup (e.g. an office or restaurant needing to buy furniture), and there is a way to account for that --- I just don't know it.