* From an economic standpoint, the US is a big enough market that it is profitable to make things in weird US units, you have 350M people to sell to, most of whom are pretty well off by world standards. It makes sense to make a line catering to them. If businesses can start making a true or good economic argument it will happen more.
* Tooling that exists in standard units seems to be a bit of a red herring: I dislike having to own wrenches in both standard and metric units - a transition to one set would actually be nice. At a larger scale, i.e. manufacturing, it would make sense to start replacing things with metric on regular maintenance cycles. With very long cycle things just having a label change.
* Paper would be a nightmare for a while - A4 and 8.5x11 are just dissimilar enough for it to be weird, and paper has a very long lifetime, dual storage systems are a pain.
* A lot of very low level infrastructure has built in assumptions about standard measure that would take a long time to convert, and some would never convert. For example, a lot of cities put roads so that $X blocks is a mile. The midwest from the air looks like a quilt - thats because all the fields are partitioned by roads which are (generally speaking) a mile apart. Land ownership for rural areas is by the fraction of a section, and by acres - it's built in to how everything is laid out. These aren't impediments but it does create a weirdness. I navigate the backroads and a lot of parts of cities by knowing how far it is and just counting how far over and how far up i need to go subconsciously, and it is an issue.
* Now is a better time than ever for doing this in terms of accessibility to the public. Everyone has a smartphone - apps to do conversion in lots of intuitive ways can ease people's discomfort.
* Car, motorcycle and other mechanical equipment manufacturers should be the people to start the transition. They can all agree to just stop using standard things for the 20XX line of equipment. Or be legislated to do so. Similarly gas stations can be required to change on $DATE, and car manufacturers can just send everyone stickers to put near the gas-hole of cars to say "your tank is $X litres". I think this would help tons. No dual labeling, just bam - it's in litres now.
* Housing things are another weird infrastructure thing: they last for a very long time. Codes are all in inches -- doors must be 36" wide, switches must be placed at 48" and so on. The sudden appearance of a second width and height for new stuff would be bizarre, or building it at 91.44 and 121.92 cm respectively would also be annoying.
I still think it's a good idea, but some thought needs to go into these weird cases that are surprisingly common before a transition would be acceptable. But like I said - everyone carries a computer or two these days, so there is probably a lot of work that could be done to simplify the transition via good apps.