Ok so I will take a crack at some recommendations. First off I would look into getting some/all of those accessories I mentioned. They will make observing sessions better and will make finding objects easier. No sense in getting a fancy eyepiece to observe objects if you can’t find them. - $47 Headlamp with a red light. There are cheaper headlamps out there but this is a nice one. I mainly use mine for camping, but I also use it for astronomy and any other time I need a light and both hands free. Get one for yourself too. I think everyone should have a headlamp. - $50 Telrad for aiming the scope at stars. - $69 8x50 RACI. Used to hop from the star you found in the Telrad to the object you want to see. Sold by various retailers under various brands. This was just the best price I saw. - $10 SkySafari 6 Plus app. The plus is the lowest tier that allows you to simulate the FOV of your spotting scope and eyepieces, making star hopping to objects easier. And the 7 Plus version doesn’t add on enough features to cost more. - The book “Turn Left at Orion”, looks like you can get a copy for ~$10.

Ok what are we at so far. $186, let’s round to $200 in case you have to pay for shipping. That gives us $200 left for some other accessories. - I would hold off on the phone mount for now. Imo he should get comfortable using the scope and observing before trying to take photos. Plus cellphone photos are usually pretty “meh” anyway. - If he wants to share a copy of what he saw, he can always try astronomical sketching. It really helps improve your observing skills, is fun/relaxing, requires very little skill, and leaves you with a copy of your observation. Search this sub for “sketch” to see examples. And check out the Cloudy Nights Sketching Forum for some really great examples. - if he doesn’t have the best back, I would spend the rest of the budget on an observing chair. They are kinda stupid expensive, here is the cheapest one I have found. All of the old guys in my club have an observing chair and wouldn’t use anything else. I am young and just use a folding camp chair, but there are other options like a drummer’s stool or photographer’s posing stool. - And finally there are eyepieces. This was just discussed so I will base my recs of that. The 32mm Q70 seems like a good budget friendly option for low power wide field viewing. For planetary viewing, the 6mm 66° “goldline” is a good option. I personally would recommend the 7mm Xcel as the slightly lower magnification might mean you can use it on more nights when the atmospheric seeing is not as good. And then get some eyepieces in between. The best budget options that are a step up from entry level are the Starguiders, I have a few and really like them. The next step up would be the Astro-Tech UWAs. If he wears glasses for an astigmatism, the UWAs might not be the best choice. - Honestly if the budget is tight, just get the full set of “goldlines” to start. They are pretty decent and could keep him happy for years before wanted to upgrade.

And finally, astronomy clubs are filled with lots of old guys that are also a bit socially awkward or anti social. You don’t have to attend everything, but there are some nice benefits to joining a club. Myself and another club member go to our local dark sky area to observe a lot. We don’t talk much, but will share the views and it is nice being outdoors at 1am in the middle of nowhere with another person. Joining a club is honestly the best recommendation I can give.