I imagine it would also have a lot to do with your long term goals in real estate.

Yes, when referring to “income is taxable to the person who earns it,” this applies to the individual performing the work, regardless of how the payment is directed.

Also, I work with a lot of long-term RE investors and none of them look at ROI.

If I were in your position, I would buy a duplex that has potential for value add, fix it up, live in one unit and rent out the other unit as a medium term rental or long term rental.

The fact that you evaluated whether to sell or do a cash-out refi shows you’re playing a long game and keeping your options open.

Some focus purely on numbers, while others look at long-term value, location trends, or creative financing strategies.For those of you investing in Chicago (or similar markets), whats your mindset when evaluating off-market opportunities?

Make sure that your area states it directly.Otherwise, let the booking site handle things. 28 days isn't that long IMHO depending on the area or reason for traveling. 

A couple of things I like to tell my newbies-Owning a short-term rental property can offer significant financial benefits.

Account Closed that's not the case as long as you live in it as your primary residence for 12 months.

Quote from @Ryan Kane: Long time follower of BP in Canada first time poster!