With no disrespect intended to BP, most of the folks I run into who use the various calculators provided here have NO real understanding of how to analyze an actual deal.Much in the way one can't become a Jedi without building a lightsaber, you won't become a confident and complete real estate investor until you can build your own analysis spreadsheet.

I have thoroughly researched market rent in my area, and I've felt confident in the price up until recently. 

If I was confident one way or another I would place my investing "bets" accordingly, but for now I make decisions based on where the data and trends suggest the most reliable chance of producing a return. 

I'm not confident in buying those and if I fail on my first attempt, I may not be able to continue confidently in the future.

However, if you are confident in your ability to find a buyer within a week, and you have a strategy for marketing the property, it could be possible.

I am confident I can find a buyer for the unwanted property but I want to make sure I am reducing my tax burden as much as possible.

On the other hand everyone has to start somewhere, so how much confidence do you have? 

Are very confident it will be covered 3. the amount paid out will be worth it. 

I appreciate the confidence boost @Bruce Woodruff!

Following David Green's Core 4 strategy (realtor, contractor, property manager, and lender) gives confidence to invest anywhere.