Nice analogy PDQ. I was in the same boat for a long time - I started out sewing first on my mother's old Montgomery Ward brand sewing machine (no idea of age). When it broke I bought what I could then afford - a Kenmore basic sewing machine. I can still use that machine for peicing and utility work, but when I started to try and venture into free-motion quilting... I think tap dancing in quicksand is a pretty good estimate, lol. That said I went and bought a much better Kenmore machine for around $600 and have been very happy with that. Free motion is not a problem, it is much quieter than the old one too. Does it have all the fancy bells and whistles of say a Bernina - no, but it does have the double blanket stitch
Point is a newer machine is probably needed at this point, but there may not be any need for the family to go into major debt for one of the really high end ones. You said they are looking at a Singer - they are not bad machines at all. If you are worried about cost though, those Sears Kenmore machines are pretty good too. I was told by someone that they are actually made by Singer, just sold under the Kenmore name for Sears. Mine is a computerized model with around 100 different programable stitches plus a full alphabet and numbers. So far I have never needed anything not already on there. I purchased a walking foot and a free motion foot and have never looked back. Good luck with your free-motion, don't give up because even an old machine can do well with lots of practice.