VETCOMMS

I bought a 24pc assorted adapters kit, plus a few SMA-M and SMA-F to PL259 and SO239 short cables, and a few PL259 to PL259 short cables. Less than $60 for all that. At this point I never run into things I can't connect to my NanoVNA, TinySA, and SW102. But your connectors are possibly more esoteric. Nevertheless you should be able to find adapters for them on Amazon, which is where I found all the other assorted adapters.

Finally got to the shed and thought I'd share the pics of the hardline.  Looks like i have Andrews 7/8 Heliax.
The NanoVNA showed and an adapter kit so next I'm hoping to learn how to put the N-type connectors on.

At high RF frequencies the signal travels along the outside of a conductor. That’s called the “skin effect.”  So, the inner portion of the conductor becomes less necessary.  

From Pasternak: In some applications, a hollow metal center conductor can be used to decrease weight and cost while increasing flexibility. Yet this solution is specific to high-frequency applications that do not need to channel high power at low frequencies.

That’s more like it.  The big one on the left in the picture is female N.  The smaller one on the right is a male N.
A local Elmer helps, but if you don’t mind us occasionally getting flustered we can help you learn some of the basics.

DX Engineering, Ham Radio Outlet, Gigaparts, Max Gain, R & L Electronics, and Amazon all have a wide variety of adapters. Until you gain more knowledge your surest option might be to go to a nearby radio dealer or amateur radio club with your radio, antenna, and transmission line and get some personalized help. 

Edited to add: no forgiveness is necessary for your lack of knowledge.  We all started out with little or no knowledge at some point in time. I think what’s making this more challenging is that you are introducing several different extreme levels of technology at once, like expensive hardline and cheap NanoVNAs.  You’re trying to determine whether hardline is good but without a background that would make it easier to discuss. We’re making it worse (unintentionally) by using jargon, or speaking in technical shorthand that probably is just word salad to you. We’re saying things that might end up costing you lots of money in tools you might not even need.
When I was getting started I ended up buying a large assortment of SMA adapters from Amazon.  I never used most of them, but because they were extremely cheap I didn’t care too much. 

So, let me back up a little:
What tools do you actually have that might be helpful?  Do you have a plain old electrical multimeter with an ohmmeter or continuity tester?  The most important tests you can initially do for a used cable of unknown quality can be done with your eyeballs and an ohmmeter:
First, visually inspect it to make sure it’s not skinned, pinched, crushed, kinked, or any other kind of obvious physical damage, Then use the ohmmeter to make sure the shield is continuous from one end to the other, Next, make sure the center conductor is continuous from one end to the other, and  Finally, put one lead on the center and one lead on the shield and check to make sure that they are not shorted together.  An ohmmeter will use DC for this test, so you should see a very high impedance, probably in the mega ohms range. Using a NanoVNA (or an antenna analyzer that covers the correct frequency range) will allow you to test more conclusively, but really, if you’ve passed the above basic test, hooking it up to a radio will tell you if it works or not. Next, let’s figure out that connectors that you included in the photograph.  You actually have two connectors screwed together in that photo which appears below.  The large connector on the bottom has been cut off the hardline. The small connector on top may be unused or may have been removed from a piece of smaller coax, possibly LMR400 or RG8, I can’t tell. The photo shows a finely knurled section.  Unscrew the knurled collar from the piece immediately below it. They should be separated at the red line. Then show us what two connectors you really have. I think the upper, smaller, connector is probably N male and the hardline fitting should be N female.

Yes. Most of the NanoVNAs have SMA connectors. I bought one that has N female connectors on the NanoVNA. 
 

The connectors do not need to match the brand of hardline, but they must be sized correctly.  The connector you showed in your picture (L5NF) was made by Andrews. The L5NF is no longer manufactured, but I would think they make something similar.  I don't know if it could be reused with the correct preparation, but it looks like it might be an N female, rather than N male. It looks like someone used it with a jumper of coax, possibly something like LMR.  I know some people are against using LMR400 for repeaters because it has two different shield metals.  If you subscribe to that theory, get M&P Ultraflex 10 jumpers; they are copper for all layers of shielding.
So, with the connector you have, with N female on the ends (male thread on the outside, but a female socket on the inside) you would use an N male to N male coax jumper.  A short jumper of M&P Ultraflex from Gigaparts will work well.
 

Before buying the connectors, see what the manufacturer has for resources for the exact connector you need.  The better manufacturers provide training videos.  Some (okay, nearly all) strongly recommend using their preparation tools, but once you understand the process you will understand what tools you really need.
Here is an example:
 

VNA is the proper way to test it. DTF and RL is the base tests I run on all lines. 

I use a pet squirrel, which is really the only scientific way to do it. He loves 1-5/8" Heliax the most. Last 700' run he tested for return loss took a record breaking 15 minutes to scale that length and come back down. Seriously, here's a video that might help. Check Youtube for other videos to get a full understanding.
 

get yourself a Nano VNA.. They're great for checking Coax, Antennas and other things..  Lots of various how to videos on Google..   https://www.amazon.com/AURSINC-NanoVNA-H-Vector-Network-Analyzer/dp/B07Z5VY7B6/ref=sr_1_1_sspa?crid=27K9G2O94D6NI&dib=eyJ2IjoiMSJ9._c0Hx-JK1n0L41oe77KD7fcLIRsFX4_XZT_H7ZxdIs8BCuulklYWSZi7bTrGHD8BF5z2nq9d8KApRHbUSVwUAgta_Ua95QfM8DPnc4-tA2DhuxMPbV3MIXo2Mx5sF585EG8W2sSQ6wvgY9C8-kgPsGcS3mn3b6tKW01ocBWjju-1rDEXX_kIkdR_YyEidg6hl9HR8HPx1PGcYOS141bEaHxJBpwGmQ8UPK5D1Dd7bYc.oIILvBvlLqcs08bDNYLGdvdRu9BbUXTzf5XOjxbRaKo&dib_tag=se&keywords=vna&qid=1725726595&sprefix=vna%2Caps%2C164&sr=8-1-spons&sp_csd=d2lkZ2V0TmFtZT1zcF9hdGY&psc=1

hamfest fleamarkets
 
 

Asking local public safety where they get their radios worked on is a good idea. 
We are lucky in that one of our club members retired from Sound Solutions Inc. and is still able to go in and use their equipment. Any business that deals with commercial radios and/or drive through systems, etc. should be able to help. It never hurts to ask.

Contact the local police/sheriff's office and ask for the name of the local company that supplies their radios.

I use the db408-b on my repeater, There is a label with all the info at the base of the antenna, but if it has been in service for years, it may be faded or missing. It is only a sticker.

I don’t know about the Commscope, but some antennas do have a nameplate like this one from our repeater‘s 2 meter antenna:

 

Yup! That's about the same as what I get.. Those small duplexers kill a lot of the RF electricities.

Yes, if they’re inverted they’ll have an I following the number usually. Of course it’s possible that the repeater manufacturer uses some other convention to indicate normal or inverted. 

Yes.

I dont have my laptop in front of me so I dont remember where you pull the model number, but YES, the Up/Download IS backwards (wrong!!) and it causes me MUCH wailing and gnashing of teeth!

You don't need an antenna just to read with the software.

Pull the config with the software.

A great feature of this software and this repeater is that to use narrow-band, you have to set your computer to a date several years prior to 2013...
You're doing it right.

Did you try right clicking on the executable and selecting “run in compatibility mode”?
Also, you can type alt+prt SCR or ctrl+prt SCR to take screenshots rather than using a camera. 

I am running CE27 V1.08 for Windows on a Windows 10 Home (22H2) .. I have it set to run in "Windows 7" Compatibility mode and it runs fine.
I am also running the same version on a M1 Silicon Mac, via Parallels running Windows 11 for ARM (64Bit), with no problems EXCEPT i can't connect/program the repeater due to driver issues with the cable and Windows 11.