John - this is one of those questions you could probably ask 10 people and get 10 answers so I'll just give you my perspective. I've been at it for about a year. I think most people would say it really depends on how much you practice. I started with GF1 and GF2 on this site and spent 30 - 60 mins a day, not much compared to many but I am in early 40's with job, wife, kids, yada, yada. With that practice time I was reasonably comfortable with both GF 1 and 2 from a technical perspective within 3-4 months. To learn a few songs I then went to You Tube and could learn a song in 1-2 days (far from perfect play, but good enough I could hear the song as I played it). So in 4-5 months I had 4-5 songs, with a ton more basic songs I could play, based on the fundamentals I knew.

For me, I felt a bit bored just memorizing songs based on the limited musical skills I had (nothing wrong with that though if that is someone wants/enjoys). I really wanted to learn the guitar so I supplemented this site with a personal teacher who has not taken me into blues and jazz....spending a ton of time on ear training, scales, new blues and jazz chords, some soloing so I really haven't learned more than my 4-5 songs but I am learning more about music.

Longer term I should be able to do alot more and do it by ear - although this is a sometimes painfullly slow and difficult approach.

If you just want to play songs though you could probably know dozens after a few months with some dedication.

Again, just my experience today....tons more of people here can give you opinions based on much more knowledge, skill and experience.