And, do you have accurate and up-to-date bookkeeping records in place so you have the appropriate data at your fingertips to be able to make strategic decisions for each property?

I thought of banking on appreciation and rate drops as pure speculation and akin to gambling.

The numbers don’t become accurate until the property is sold, anyway.

However, the remaining gain not covered by the Section 121 exclusion is taxed at your ordinary income tax rate.Here's how the calculation typically works:Calculate the Depreciation Recapture: The $9,000 of depreciation would be recaptured at a maximum rate of 25%, which is $2,250 (25% of $9,000).Calculate the Remaining Gain: Subtract the excluded amount (Section 121 exclusion) from the total gain: $100,000 (Total Gain) - $9,000 (Depreciation Recapture) - $250,000 (Section 121 Exclusion) = $0Tax the Remaining Gain at Ordinary Income Rate: Since the remaining gain is $0, there would be no additional tax on the gain.So, based on this calculation, it seems like there should not be any additional tax owed after taking into account the Section 121 exclusion and the depreciation recapture at a maximum rate of 25%.It's essential to review your calculations and ensure that you are accurately applying the exclusion and depreciation recapture.

Knowing the property's condition helps you accurately estimate these costs.

When I checked out Google Vacation Rentals when it first came out, the data was not super accurate, so I'm hoping they keep building out that aspect! 

We need more information to be able to accurately answer that.

I have seen sites like CreditKarma or Credit Cards under-report and over-report consumers scores, so they are not the most accurate.

If you have $100,000 in your brokerage account to borrow against, why not just use the money and secure a traditional loan, versus gambling with an unknown and variable future rate?

For a more accurate valuation, I’d recommend reaching out to a local realtor or hiring a professional appraiser.