I have the Harley Digital Oil Temp Dipstick. One word, awesome, love it.
I read reviews from the past, some good, some not so good, well I guess they are way improved from years ago or I am one of the lucky ones but its now over two years old and still working great, I havent even needed to replace the battery yet and I am thinking of changing the battery "just because" it has to get low sooner or later. I am always checking the oil temperature with it and amazed the battery is still good.
Its also accurate as I checked the digital HD gauge with a food grade candy thermometer.

I first, like you, tried to save a few bucks and bought that JES Customer oil filled analog one, I also like the idea of analog. The JES failed within 2 weeks. I bought the oil filled one and the darn oil leaked out. Anyway Im not knocking JES as they did honor their product and refunded my money or whatever store I bought it from, it was years ago.

The HD digital gauge has been working perfect and I have found myself always buying HD stuff now, lighting ect. I dont know, people say their stuff is overpriced, all I know is everything I seem to be buying is priced around the same price as after market stuff and the HD stuff hasnt let me down.
Plus it's screws down just like the regular HD dipstick.

I say just go for the digital HD gauge, no matter what others say, its what makes you happy just as others might buy accessories that make them happy but not needed. Since I learned that 2 up, high speeds produced the highest oil temperatures, instead of adding a fan to my HD 6 row oil cooler I upgraded the oil cooler to a 10 ROW Jagg cooler, again, just for fun.

I also installed Lenale fan for those Beach traffic days. It's simply replaces the horn and I think looks better too. It will cook your legs when you turn it on but it is what it is.

I love knowing what my engine is doing, love information, we do a lot of interstate, to the mountains, to the beach, sometimes sit in traffic at the beach or wide open roads into the mountains, I bet a lot of people dont know, some of the highest oil temperatures are at high speeds! I love information like this.

So I can bet all the people who dont have a gauge do not know this! Then they wonder way there is no fan for the oil cooler built in! Because the oil temperature is actually higher at high speeds when air is already flowing through the OEM oil cooler, fan not needed and not helpful at those speeds! Like hello?
True, stopped in beach traffic a fan would help but not really effective cooling the engine and your better off with a head fan at that point (which I have) because you NEED AIR running through the heads.

This is the one I have, worth every penny to me and the price isnt bad, https://www.harley-davidson.com/stor...10-6300409a--1

 

HD has fixed that issues of the old model. I had one and the LED numbers went wacky, others have had issues with condensation. However, I did get another one year warranty from Boardtracker on the new one

I have the new one, and it looks cool. However, I have it because of the convenience of checking the oil at any time or seeing the oil temperature as well. It is a convenience item and it is expensive. Eventhing HD is, everybody has an opinion on this forum including me. However, I try to listen to the post that actually address the the OP's question, not offer said advice without any experience.

https://www.harley-davidson.com/stor...10-6303009a--1

 

Had two of the older digital Harley oil temp gauges that lasted two or three months and failed, Bought an analog oil filled gauge from JES Custom Accents that I've had on the bike for almost 3 years now and it works perfectly. The JES unit is of excellent quality and was reasonably priced at the time.

 

Just my experience on 2 HD digital gauges. HD, or their maker, may have improved them by now but they fooled me twice.

No experience on the oil filled JES gauge, but the non-oil filled. Been working great for me for 4 years now.

 

I have the analog one since 04, still works fine. Had to add one o-ring in the stopper groove to tighten it up. Still has one groove left. That should carry it for a good 28 years...In a pinch, you can use it to see if you have a temperature. Comes pre-lubed..

 

Had the original HD LED, failed after a year. Bought a used JES oil filled dipstick gauge here on the forum. Previous owner put 20,000 miles on it before moving to M8. I have 3,000 miles on it. Works great and still looks brand new as well.

 

I have this air filled oil temp gauge on my TriGlide and it's accurate and well made. They also carry an oil filled gauge but some people reported leaks with it. They come in white or black face.
https://www.jescustomaccents.com/Bla...Gauges_c37.htm

 

got one two years ago, love it.

 

I have the Harley one, works great and has for 7 years now. It is nice to know the temperature but I don't worry about it. It is also a quick and easy way to check oil level, just have to press the button and you get temp and oil level. very easy and worth having in my opinion.

 

Instead of the gauge, put the money towards an oil cooler if your bike doesn't have one. Really made a difference on my '04. I don't worry about the temp of the oil, it's running cooler now. You could get a Jagg Slimline oil cooler for about twice the price of the gauge. Good luck.