Tokyo Town Zone is just.....well dumb.

Well the Tokyo Town feature is not easy but it is not as dumb as you thought. Here are two suggestions to help you out.

First the Tokyo Town items (cat, lantern, etc) can also be found through City Rewards. Essentially you visit other cities and collect free rewards. Most of the rewards are common items but sometimes it can be cash, gold key, or even Tokyo Town items. I did not play this game often when I use City Rewards causally I can find at least two Tokyo Town items per day. If someone has a bit more patience and time, I think the reward can be exponentially higher.

Second you can ask the Tokyo style building to constantly redesign until it fits the items you have. This is time consuming though.

Resetting designs is a work around, also visiting cities and popping bubbles has given me quite a few Tokyo items.

I totally agree, I get close to quitting so many times, because they love to utterly frustrate a person. Games are supposed to be enjoyable and fun.

the problem is that you are starting a TT as soon as you have 1 Tokyo item. It's not any different than London or Paris it just takes longer as it should since the population boost is higher. If you are that ancy and you only have 1 or two TT itme, just request new plans (30 minutes) as opposed to waiting 18 hrs for a new plane.

Although it has taken me as long as 4 hours for the item to be the item I need by requesting new plans.  It often gives you the same one over and over.  That is only mildly frustrating though.  I normally don't care how fast I upgrade those areas, just that they eventually get done.  I'm only doing 10 of each and no more though.  Just the bare minimum for the requirements of certain landmarks.  Paris and London are already fully upgraded.  Only working on TT now.  Only 3 more buildings to go or 5 upgrades to go then it will be done and I will not be placing any more.  

Once all 10 of each are done the special items/airport items then becomes pure money.  I've already been selling off Paris and London.  The London ones are 2000 each.  Have 5 of them?  That's 10,000 in the bank.

I'll only do more than 10 if there is an update that will allow them to produce speedup tokens or something else that would be beneficial within the game.

You can usually buy those tokens in the Global Market.