How to have fun:
What a deep philosophical question 😉 . I would like to suggest 3 general things:
Firstly – in any hobby it is generally possible to buy almost anything for any amount of money. Model trains – how about this starter pack for 10$? Or this original steam engine driven unique for 10.000$. This kind of fun usually wears of pretty quickly (or if you already regret your purchase once it arrives it may be rather a sign of compulsive buying). One solution here may be to learn to “fix” or later even build your own things. Deliberately buy broken things and see if you can get them working again. If successful it can be a rewarding experience (but can also be difficult and at times feel like work).
Secondly, I am convinced that DOS era and older PC games really are something special and there really are a lot of gems that are worth exploring even today – without any nostalgia. However, this too needs effort. I recently read that TV programs are adjusting to parallel phone use. If that’s the effort you want to put into your hobby / entertainment, then I can’t see this working. Otherwise (as already suggested) – why not explore games from an era slightly before your current interest.
Instead of the Sims – try “SimCity2000” (also a Sim, or if you want more action – X-Wing)
Instead of Duke – Try “Fate of Atlantis” (also snarky dialog and action – if preferred)
Instead of Quake - Try “Eye of the Beholder” (Also in 3D !)
The experience may include a steep learning curve and can be anything from difficult, frustrating, to amazing. Altogether though, especially if you if you stick to the end and beat these games - this too can be fun. (I am currently educating myself on classic arcade games - well before my time - Im at level 54 in Galaga, Level 14 in DigDug and already beat Outrun – and yes – I am having fun) In general this second suggestion does not really require any real hardware. Emulation / GOG etc. is usually a much easier approach.
Finally – there is the “Original Game on Original Hardware”. Imagine you are taking a trip by plane. In 99% of the cases, you will enter the plane via a boarding bridge where you may not even see the plane. Sit down in a seat just like in a bus with an overall similar experience. Compare that with an open 2-seat plane where the pilot is starting the propellor by hand (i.e. an XT PC). Now think of the noise (mid 90s CPU fan), the smell (blown capacitor) and the time such an old plane needs to get from A to B (loading your software form tape). Why would that be fun?