Tell me if this is stupid: home charging solution

So I don't have a driveway or any off street parking. I park on the street in front of my house. There is a sidewalk and median separating my front yard from the street.

Initially, I was charging at a public station 2 blocks away (free!), but it's often in use and I got sick of the hike.

Currently, I am running an extension cord from my 120v outdoor outlet to the car, and plugging in the slow charger there. Where it goes over the sidewalk, I push it into a groove between pavers and put a heavy rubber doormat over it. This works, but takes forever to charge. 30 hours? I have seen other people with engine block heaters hooked up this way, and so far no one has hassled us.

- My plan is to add a 14-50 outlet on the front porch on a 50 amp circuit.
I found these waterproof intermatic outlet covers: http://www.intermatic.com/~/media/intermatic/documentation/weatherproof_products/wp_brochure.pdf?la=en

- Then, I will buy a Jesla to plug in on the porch, and a 40ft Jlong extension cord to run over the sidewalk and plug in at the car.

I'm trying not to draw any attention to the project. I should technically get permits etc. but I worry they wouldn't approve it because "running an extension cord over the sidewalk" can't possibly be a reasonable request. And what other purpose could a 240 volt outlet outside be for? This is all going to cost $1200+ for the electrician, plus $1000 for the Jesla, and $400 for the Jlong. If the city calls us out, we might have to undo the work. Any thoughts?

Questions:
- Is it safe to leave the Jesla plugged in all the time?
- Or should I unplug it between uses, esp in bad weather?
- I'm not sure there are any waterproof covers that will enclose the plug on the jesla?
- Will repeat plugs/unplugs cause problems?
- The J1772 Plug Holder (Wall Mounted) receptacle looks useful; but what kind of wall hanger would you recommend?

I know there are a number of more elegant solutions, all of which involve burying conduit and installing a power post (like http://www.intermatic.com/en/products/weatherproof/specialtycovers/outlet_post). I can't see installing a post on the median as I don't technically own that land and it seems more vulnerable to city interference. I could install a post at the edge of the lawn, but again, that requires digging, and would be more visible to the city than an outlet attached to the house when not in use.

Looking at how other cities do it, Berkeley has (I think) a terrible, convoluted pilot program for median charging stations, but only if you don't have room for off street parking (we have room; just don't want to lose my yard):

http://www.cityofberkeley.info/EVcurbside/

This person installed a public charging station on their curb in Palo Alto, but they jumped though a lot of hoops with the city:

http://projectgreenhome.org/?page_id=17

Technically Boulder supports EVs and has some free public stations, but I've emailed multiple people associated with the program about charging on the street and never heard back. One of the stations has been broken for 6 months or more. So I'm thinking funding is light.

Is there anything on the parkway to distract from having a pedestal? Such as a mailbox on a post? That would be my choice.
Doubt the city would ever know unless someone calls you out.

Definitely call an electrician. They have seen it all before and can give best advice for your conditions.
Trench can be dug and buried in one day. or Put a flower bed in and while the gardener has it dug up just drop in the direct burial wire.
Use a drill to get under the sidewalk. yes there are drills made for this purpose.
Plant a bush or something appropriate to camo the termination.

There was recently a thread about an almost identical situation over at the Leaf forum: http://www.mynissanleaf.com/viewtopic.php?f=26&t=21404

Long story short, you could make it work, but running a cable over the sidewalk is bound to cause problems. And do you really want to have over $1000 in equipment just left out like that all the time?

My advice to that poster was to go ahead and dig a trench, but just install an outlet near the curb rather than a fancy pedestal-mounted EVSE. I don't recall what he ended up doing, but I think he said he was probably going to move. And that's really the best solution - it's hard to make an EV work without a dedicated parking spot of some kind that you can run power to.

Well I did it. I mounted the plug to the side of my porch. I also ordered a cable hanger from clipper creek. Cross fingers! It takes a lot less time to charge now so maybe it will be less visible/less of a nuisance. Maybe I can add a lock/chain to the Jesla/Jlong to keep it attached to the house. There are also small locks on the holsters to keep them from walking off. A determined thief could take it, but I hope there isn't one of those. If it gets stolen, I'll probably have to get a cheaper charger, but would still need the Jlong.

I use a JESLA to charge at home and I have an 14-50 outlet on my front porch as well. The JESLA is secured to the wall via a couple padlocks, a chain and eye bolt screwed into a stud. The actual body of the JESLA just sits in a holder and the chain is wrapped around the cord. The cord holder is the white one used from a Schneider Electric EVSE. I was hoping for something more secure but I haven't come up with it yet. I also have to use a JLONG to get enough length to reach down the driveway. I may someday switch to a wall mounted EVSE when I find a good deal on one.

Glad I'm not alone! I figure down the line I can be bold and extend the line to an outlet on the median itself if I find a willing accomplice electrician. Just have to avoid all the buried gas and sprinkler lines, which is kind of an impediment. This current solution is just lower investment at this point, even if it's a bit of a hassle to rehang 50' of cable.