6 years ago I decided to succumb to severe mental illness and get a hack.
Having never driven one I knew from+ years of motorcycles that I was more than likely to beat the crap out of at least the first one. I got a $3000 1996 ural italia, With my faithful canine companion, Gus, I set out to terrorize the roads and backways of N Fl. We ran dirt roads, smashed the chair fender into walls, posts and small trees, blew the cylinder head across a 4 lane highway ( it kept running and got us 500' to a safe pullout), I am in agreement with all uralists in that it is a RPOC. it'slack of power was only exceeded in its inability to stop.
So after about a year of this silliness, I traded it in on a 2003 Retro ( told you, sever mental illness) with ~15000km on it. It now has 49000. in the last 5 years Gus and I have ridden it to NC, done the "tale of the dragon several times", suffered the main street crawl at bike week. In the last 5 years I have had the alternator go bad and damage a timing gear. The alternator I got rebuilt at a local alternator shop for $40, the timing gear had to be replaced at the dealer $200 P&L, How much would the bill be to replace the timing gear/chain/etc in your ride? Owning a Ural means you will have an intimate relationship with routine maintenance, If you're the type who takes his bike to the shop for oil changes then a Ural is definitely not the bike for you, but then neither is an airhead, Norton, or Enfield
Recently I took delivery of the all american rig I have been working on, Victory Classic Cruiser for the tug and Clark Stanley Motorworks chair. The first thing I realized was just how well the Russians set up the rig.
1 No head shake
2 very slight pull right on acceleration, none at speed
3 brakes applied properly, no pull left even on panic stops
Eventually I will have the Vic rig set up the same, But I have the advantage of the Russian standard as to what is acceptable handling.
Bottom line is
If you can't or won't take the time to do 90% of the work on your bike no Ural for you.
however, If you want to learn how to drive a hack and not be worrying if its weird or just normal sidecar weirdness, or even if you really want a hack. Get a post 2000 Ural before investing $30k on a full rig