Are there any secrets from experienced travellers on how to book multi city breaks inexpensively?

Question

(Possible duplicate of this, but due to it being over 10 years ago, I'm hoping things may have changed).

I live in the UK and I had two conferences a week apart - the first one in Las Vegas, the second in Orlando.

Getting a return from Orlando was ~£500, and getting a return from Las Vegas was ~£750. To get a multi city/single ticket was going to cost me over £1,700!

The Las Vegas <> Orlando leg was approx. £120 each way with luggage.

I saw that my plane from London to Orlando had been only late once in the past month by 10 minutes and was early nearly every day, so, I figured a 4 hour gap would be enough.

To get straight to it - we landed early, but, by the time I picked up my bag and gone back through security at MCO, I actually arrived at the gate after closing - thankfully there was a queue of people and I managed to get in.

I'm trying to experiment with ITA Matrix right now to find more combinations/codes, but, failing!

To me, this just felt crazy - Looking at cheap carriers (Spirit/Frontier etc.), they had passes on the day for not "that" much more than I paid, so, I was just wondering - what is the "correct" way to handle this?

1. Pay the heavily increased multi city ticket?
2. Do what I did, gamble on arrival time - maybe leave a bit more time?
3. Is there any insurance available on the above? I couldn't see any option.
4. Book a day either side, get a hotel?
5. Buy the connecting flight on the day/after landing?
6. Other?! - here to learn!

Answer 1

Often the best solution here is an open jaw ticket for the trans-Atlantic flights (I just searched for London to Las Vegas and then Orlando to London on random dates next month, and there seem to be plenty of options at around £750) and then buying the domestic flight separately. As each of your flights would be separated by several days, there's no risk of getting held up and not being able to catch your flight home.