Retirement tax questions

Here's the data! I tried to do this myself but got a different answer every time. I have a new calculation but would love to make sure it's correct. No distributions from traditional IRA other than conversions to Roth. 

Goal is to determine how much of my traditional IRA i should convert with the lowest tax implications (now and future), when I should convert, and if I should resubmit any 8608 (i.e. 2017). 

I am also not sure why the current value of my traditional IRA is so high. but it is invested as a single account with some other investments (Betterment) - the FMV might be lower when I get my statement at year end.

 

Calendar YearTraditional IRA ContributionsDate of ContributionConversion to Roth IRADate of ConversionYear End Traditional IRA Value
2015$4,500.0009/03/15   
 $940.019/21/15   
   $5,407.279/21/15$0.00
2016$1,000.003/22/16   
 $400.006/28/16  $1,518.29
2017$3,300.00 (2016 tax year)2/21/17   
   $4,899.943/1/2017 
 $2,000.0003/21/17   
 $1,000.0012/01/17  $3,047.43
2018$2,500.00 (2017 tax year)03/08/18   
 $3,000.0003/12/18   
 $2,000.0010/15/18   
 $500.002/27/19  $9,652.86
2019$500.0001/07/19   
 $500.0002/27/19   
 $3,000.003/18/19   
 $2,000.0003/01/19  $18,066.47 (current value)