The UV-5R(G)(X) series of radios is an excellent "gateway" radio into a lifelong struggle of buying newer, bigger and better radios to meet your needs!
Others will chime in, but most HTs use an SMA connector.
the gender is determined by the post or hole in the middle, not the threading.
Each adapter will generally cause some loss of power. But I use them when needed.
If chatting with your buddy is your primary objective and you can be line of sight with that altitude, get a couple of 50 watt Wouxuns and high-gain Yagi antennas aimed at each other and chat Simplex on the High Power channels.
I purchased a Baofeng UV13-PRO (the Ham Radio version of the UV15-PRO for GMRS) for $20 including shipping from AliExpress and it seems to transmit on GMRS as well.
USB-C battery charging, too!
I purchased a pair of Pofung BF-T11 FRS radios from Amazon and one had bad audio.
Amazon sent me two more and told me to keep the originals, so now I have 3 good working ones.
Yes I am not receiving it in the Eastern San Fernando Valley.
I will refrain from posting this comment in all the other Mesa Crest posts that you opened.
More negative chatter about Midlands.
They seem to be helpful to the Jeep crowd, going off road and having friends buy last minute FRS radios at sporting goods stores and Walmart, to use as well (hence why the Midlands are narrow band).
You can monitor two frequencies at a time and scan VHF/UHF (500 channels).
I believe other threads here make the claim that 40 watts does not enable that many more “fars” over 20 watts; antennas being more significant.
I personally like the $99 - $109 Radioddity DB20-G a/k/a AnyTone AT-779UV 20 watt mini mobile with everything on the mic, cigarette lighter plug and a cup mount (or here) and $20 mag mount antenna for easy in and out in my car and I have another one in my home.
And I avoid all the Midland problems I read on this forum.