I got my first sewing machine ! Here's my experience so far:
The machine is a Singer 66 converted to hand crank and bought on ebay, it was built in 1912, that's right, my new machine is 103 Years old !
Price wise it cost $180, so under my original budget of $300 , the recommended Singers (The 4411,4423,4432) in comparison retail for around $140.
So far I am thrilled, as an Industrial Designer it feels more like a lesson in early manufacturing and how things were made to last ( Originally though it was expensive, like 6 months worth of savings expensive, or about $1,100 in todays dollars), it is also highly recommended for sewing canvas/leather, it is easy to repair ( I partially disassembled it already and fixed some minor issues), has a high resale value (even if rusted/a lemon) but do try getting one serviced from a pro , as a plus it is whisper quiet and I like looking at it, the not so nice is that it lacks features like auto backstitching, precies stitch length and other modern conveniences, it also looks it's age in some parts, but for starting out I think it is a decent choice.
I also considered the following : Singer 12k , Singer 99 ( sort of the same deal) Singer 201k mk2 ( manual and motor versions) supposed to be amazing, but hard to get. Singer 306W, killer industrial design, maybe my next. Sailrite, expensive but awesome, maybe one day.
All in all a great experience so far, but will update if I change my mind or go for a different type/model.