I've taken your example and added some random values so we have something to work with:
df = pd.DataFrame([[1, '3/10/2002', '4/12/2005'], [1, '4/13/2005', '5/20/2005'], [1, '5/21/2005', '8/10/2009'], [2, '2/20/2012', '2/20/2015'], [3, '10/19/2003', '12/12/2012']])
df.columns = ['id_num', 'start', 'end']
df.start = pd.to_datetime(df['start'], format= "%m/%d/%Y")
df.end = pd.to_datetime(df['end'], format= "%m/%d/%Y")
np.random.seed(0) # seeding the random values for reproducibility
df['value'] = np.random.random(len(df))
So far we have:
id_num start end value
0 1 2002-03-10 2005-04-12 0.548814
1 1 2005-04-13 2005-05-20 0.715189
2 1 2005-05-21 2009-08-10 0.602763
3 2 2012-02-20 2015-02-20 0.544883
4 3 2003-10-19 2012-12-12 0.423655
We want values at the end of the year for each given date, whether it is beginning or end. So we will treat all dates the same. We just want date + user + value:
tmp = df[['end', 'value']].copy()
tmp = tmp.rename(columns={'end':'start'})
new = pd.concat([df[['start', 'value']], tmp], sort=True)
new['id_num'] = df.id_num.append(df.id_num) # doubling the id numbers
Giving us:
start value id_num
0 2002-03-10 0.548814 1
1 2005-04-13 0.715189 1
2 2005-05-21 0.602763 1
3 2012-02-20 0.544883 2
4 2003-10-19 0.423655 3
0 2005-04-12 0.548814 1
1 2005-05-20 0.715189 1
2 2009-08-10 0.602763 1
3 2015-02-20 0.544883 2
4 2012-12-12 0.423655 3
Now we can group by ID number and year:
new = new.groupby(['id_num', new.start.dt.year]).sum().reset_index(0).sort_index()
id_num value
start
2002 1 0.548814
2003 3 0.423655
2005 1 2.581956
2009 1 0.602763
2012 2 0.544883
2012 3 0.423655
2015 2 0.544883
And finally, for each user we expand the range to have every year in between, filling forward missing data:
new = new.groupby('id_num').apply(lambda x: x.reindex(pd.RangeIndex(x.index.min(), x.index.max() + 1)).fillna(method='ffill')).drop(columns='id_num')
value
id_num
1 2002 0.548814
2003 0.548814
2004 0.548814
2005 2.581956
2006 2.581956
2007 2.581956
2008 2.581956
2009 0.602763
2 2012 0.544883
2013 0.544883
2014 0.544883
2015 0.544883
3 2003 0.423655
2004 0.423655
2005 0.423655
2006 0.423655
2007 0.423655
2008 0.423655
2009 0.423655
2010 0.423655
2011 0.423655
2012 0.423655