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,).

Time your purchase.  1,600 square foot ranch,  Entire rooftop balcony, mahogany furniture and doors, marble top kitchen and bathroom, tile floors, double pane glass, porch, plastered inside outside.  5 foot diameter trees around .  

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.

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

You can only get the depreciated value of the furniture. 

However, I don't think there's a big demand for only half-furnished places -- homes with furniture but no silverware.

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.

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.  

I use my car for shopping for properties and furniture!