This topic has been discussed at length several times before, I'd recommend doing a site search on this topic. I've got a lot of data gathered concerning available gear ratio combinations to tailor the 4 speed VW transaxle to the available power band of the motor. It is possible to get this perfect without resorting to a 5 speed, but it will require some aftermarket gears.
Firstly, the stock R/P for a Beetle is 4.12- the 3.88s were stock on Type 3s I believe. When you order a "standard" transaxle, the gear ratios are: 3.78 first, 2.06 second, 1.26 third, and .89 fourth. There are two different ways to get a "freeway flier"- one is with a .82 fourth and the standard 4.12 R/P, the second is with a standard gearset and a 3.88 R/P.
For a 1776/1914, the 3.88 with the stock gearset is a decent choice. However, there are some generalizations that can made. Firstly, first gear is way too tall for anything other than full-on drag racing. Secondly, the spacing between third and fourth is too close. These ratios were compromises that VW made to compensate for the fact that the original engines were underpowered- the tall first was get the car rolling with an engine with no torque, and the close 3rd/4th was because the engine wouldn't pull the car up a hill in 4th.
A speedster is quite a bit lighter than a Beetle, and has shorter tires generally. In addition, almost all of us run something bigger than a stock 1600. All this works together to make the gear selections frustrating, and poorly spaced. What good is that 2110, if the power doesn't make it to the ground in an optimal manner?
A bigger engine will need some custom gears to make driving the car a good experience. It will also require the "pro-street" treatment that was outlined above. $1500 will get you pretty much everything you could want- custom ratios, hardened keys, welded gears, heavy duty diff and side plate.... everything. Less will be a compromise.
Bill- When you use the calculator, its good to know where your engine is making power. I don't know what you've got, but shifting at 5000 rpm, and dropping to 3000-3500 rpm would be about optimal. This keeps you in the heart of the power band for most larger engines. You can calculate where exactly that is by plotting how fast you are going in any ratio at a given RPM, and then finding that same speed in the next gear- that will be the RPM drop on the shift, because the car will be moving that speed when you shift.
With even shorter tires than the 165/65s most of us "classic" guys are running, I can imagine your gearset is too tall. I'd definately do something- the 3.88 with the stock gears would be a start, and it's cheap. More money gets you better spacing- call Rancho and get a catalog (they're free).
As far as your speedometer problem, one of the speedometer shops in CA will be able to fix that for you. Good luck.