Debra bug(s)
Another tip to those who want to avoid hours of wasted efforts, do not talk to Debra at the Beach at all, it causes the "need to close down game bug".
Instead talk to her in the evenings at the "Mall", same dialogue (depending what stage your at with her), but with no bugs as far as I can tell.
However, be smart and patient.. not like I was... Do not approach her before you have talked with Jonathan about everything else but her.. as in talk with him each day at 11:00 on the beach, do the topics from top to bottom and the last thing you ask him, is "about that woman you saw him with". Doing it any other way may very well mess up the point gains for Debra and possibly ruin your investigation path about Jonathan, breaking progress with Cheryl.
Here is how I stumbled upon my game mistakes...
The first thing I asked Jonathan about was the woman (Debra), then I could suddenly talk to her, wasn't possible until then (Doh.. of course not), but she didn't really want to talk as Snake is a stranger to her.
After some time I did some work in the Garage, at that point in my game I mainly earned money through Bouncing / Drug selling, but happened to need more cash so went to the Garage in the morning and suddenly Debra needed her car fixed.
Doing that created her face picture on my Stats lists with 4 points to it, now she was more willing to progress our dialogue but as I wasn't finished with my Jonathan conversation topics, I went ahead and talk to him again. The topic of Debra was gone from this list of topics, all others remain even if asked I before I think.. anyways, as soon as I had talked to him again, Debra's face picture was gone.. "Oh no!" hours of playing around I found I could talk to her, but no progress and no picture return.. until after something I don't recall atm.. but point is the picture returned, with 0 relation points.. and I was able to drink with her and take her back to the nice Hotel, which I had paid 500 bucks for a week.. she refuses to go to the crappy place.
Anyways.. her points remain at 0 and didn't seam a way to (re)gain progress regarding her, Jonathan or Cheryl.
So once again: Do all the other Jonathan topics first, from top to bottom, after asking about "The woman I saw you with" wait for her to show up in the Garage, could be you need to approach her once, either at Beach(afternoon) or Mall(evening) but Beach will bug badly so be ware.. only do this if she doesn't show up for car repair.
She can also be found in Cheryl's hair saloon shop for more/other dialogue's, Tuesdays at 11:00-17:00 I believe it is.
Regarding Cheryl, to those who wonder if it's possible to earn relation points with her and how:
Yes it is!! What it leads to I do not yet know, but buy a bottle of wine at the Mall, wait till she is home alone and you are at a certain stage in your investigation regarding Jonathan I think.. am pretty sure the option to share the wine with her first opened up after I told her that Snake saw her with another woman and that she should be careful.
Anyways.. from then on, each time Snake drank wine with her she gained a point, got 11 there so far, but no progress (which I suspect has to do with me messing up the Jonathan/Debra convo/event order *sigh*).
A new bottle shows up in the Mall, for 30 bucks, right after it's gone from inventory, as in shared with Cheryl, so could say it cost $30 per Cheryl relation point, up to a certain stage I guess.. will have to restart and play everything to be certain, which is gonna wait a while.. or maybe I'll just wait with restarting until the game is finished.. am not sure yet
That's my discoveries for tonight, hope some found it useful, maybe even entertaining? Cheers all