Tax Advice for Flipping

[David Johnson]

Aloha everyone!  I hope all are doing well during these unprecedented times.  I'm looking for quick tax advice on how to file my couple flips and really appreciate your time and knowledge!

General info: I purchased the two properties in 2019 with the intention of flipping under my single-member LLC. I plan to do maybe 1 or 2 flips this year (2020), but we'll see how this economy goes.

Property #1: Purchased in 2019, flipped, and sold the same year for a slight loss of $10k (held the property for less than a year)

Property #2: Purchased in 2019, flipped, and planning to sell in 2020.  (will end up holding the property for more than a year)

Questions:

1. What's the best way to file this?  Do I have to file a Schedule C of 1040 or Schedule D of 1040?  My main concern is that most of my expense for Property #2 is in 2019 and income will be in 2020.  I want to make sure I realize Property #2 P&L in the same tax year.

2. Since Property #1 has a loss of $10k, will I be able to claim those losses?  If so, does it matter if I use Schedule C or D?

3. Depending on how I file Property #2 for 2019 taxes, what could be a negative impact if I chose to convert Property #2 to a rental in 2020 and hold for the long-term?

Thank you so much and Aloha!