Just having a quick look at the odds, and they sort of reflect the previous discussion on here.
Liam 4/9 vs 13/8 Jack 4/6 vs 11/10 Ryan 4/6 vs 11/10 Evan 5/4 vs 4/7 Jan 4/1 vs 1/6 Mark 9/2 vs 1/7 Aidan 6/1 vs 1/10
So 3 sizeable underdogs and 3 almost 50/50, with Liam a bit more of a favourite. I think the draw is pretty fair overall, could have been far worse.
While Jack and Ryan didn't advance, Liam obviously did and he was the clearest favourite out of all of them, and I've just seen the odds for his next match against Griekspoor and it is 4/9 (Liam) vs 13/8 again, so hopefully that's an omen and he can advance to the FQR.
Just looking up the prize money for qualifying its gone up quite a bit the last few years. Now £7k for 1st round exit. Not a bad days work for some of those who managed to get a Wc. Liam earned himself an extra 6.25k with todays win. Get to the final round of qualifying and you get £22.5k.
That 7k for playing will Im sure come in handy for Ryan, Mark, Evan etc... for being able to book trips for tournaments. Evan of course is also lucky with a doubles WC. 1st round the doubles in now 12k, so an extra 6 for Evan.
For comparison to Evans career to date the £13k or $16k is roundly 25% of his total career earnings on the tour. According to the ATP site he has earned $59k.
But no, you wouldn't be able to get a second entry to the same competition. You could only proceed as a LL, if there are withdrawals from the MD before the start of the tournament.
And to be fair, it is v unlikely the event would wish to offer a WC to someone who was beaten earlier in qualies even if they could. I suspect most events wouldnt be too bothered at giving places to Lucky Losers as it is slightly awkward when an LL ends up winning the whole thing (although it does create a story) but they are sort of forced into having no choice by the rules and regs in pro tennis