I'm not a great guitarist, amateur at best - however singing and playing was something that I picked up quite early... hitting the right notes with the right instrument was always a problem at first, especially when the keys went for a wander, but my timing was usually pretty good.
My technique was 'logical' I guess, the first songs I wanted to learn on guitar were my favourites to sing and bop about to - the timing was there for me already lyrically, and it helped me to keep the timing on the guitar right - I'd know instantly if I messed it up.... usually...
Again with no formal training in either discipline, I relied on circumstance and the easiest but most demanding option... my partner at the time was a fantastic singer, and so we informally developed the following strategy...
I'd put the song on that I was learning... nose down in the tab, listening to the guitar and following the patterns and chords (with the amp off)
She'd naturally begin to sing, so I'd progress from playing along to the recording and start playing along to her, joining in the chorus's (the easy bits! lol) - her own vocal tonality, accent and emotions almost retimed the song, and gave me room to add a few extras or play with substitution... And when the track ended she'd often pop back into a chorus...
Eventually when I'd almost nailed the song, I'd start playing through the amp, without the cd- she'd start singing, and I'd join in where I could... Choruses, easy parts of verses...
Before long I was singing the whole song... whilst playing. Now I just need to get a voice capable of matching the beauty of the guitars!
Shame we're not still together - could be busking in Durham market place by now! lol
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) It helps with your multi tasking. Or if you don't have many friends just try to focus on something else besides playing your guitar while playing a song, ex do simple math problems crap like that helped me. 
