Hi Loquai, it's always a difficult decision to make when it comes to buying a machine, mainly because when you're coming from handstitching there is no one machine to replace it. A manual machine, like the Outlaw, will be the closest because it can handle reasonably heavy thread on somewhat lighter materials. There are doubtless many who have used them successfully but also many who have had issues due to their inherent limitations. Having only one hand free is likely to be the major issue. As has been suggested a good used Consew (or equivalent) fitted with a servo could be a good way to get started without breaking the bank. If it works out you'll likely start looking at a second machine, something that will handle heavier leather/thread. Just warning you, it can be a slippery slope this sewing machine thing.