Also, what others have said, the personal touches on what is in your place (e.g. providing all the essentials instead of having people buy TP, coffee, shampoo, etc.) and the quality of those items (no tattered towels, stained sheets, etc.).  

I am an aspiring new real estate investor based in CT looking to use the power of real estate as a wealth building tool and income producing asset class.

What is essential to me is to understand  one piece of transaction I discussed in OP.

LLC's are still the way to go but yes you can't tap into owner occupied mortgage tools such as HELOC's or high leverage.

They are essentially the same thing you are describing, but sharing an "expert opinion".I am also not a fan of how BiggerPockets itself is doing this same thing in the forum by posting blog posts and you don't have the ability to comment on the posting (because some times I disagree with the posting!) 

He's essentially lost $150K.Run the numbers if he was renting it for 5 years (minus mortgage, property taxes, repairs, etc). 

Is it from experience of there are tools out there that show numbers on specific areas?

It appears to hold much year round potential with the right tactics and tools.

Be sure to check out the free tools BP provides to help analyze deals you may have and also market insights.

Tools like QuickBooks or even a simple spreadsheet can help you mentain compliance and prepare for audits.Reinvest WiselyScaling a short-term rental business often requires reinvestment in marketing, property upgrades, or even hiring help.