How to best approach my "guy" to pay - Please give insight

This is a legitimate question. 

Background I am a 29 yrs old and a full time professional in which I work for a major University.  I aspire to climb the University ranks.  I am recently engaged and am no longer completely fat so life is good haha.  I share this because I think it is important to know when potentially giving me feedback. 

I have lost A LOT to this particular bookie over the past few years.  I am probably down about 15k total to him over that time frame and always paid him as I don't bet what I can't lose.  I call this time period my learning curve.  

Now my bookie is not actually someone who I have ever met.  I am from New Jersey and currently live in the midwest.  We have a mutual friend and I put my bets in through a third party site and square with him based on that.  Usually I just square with the mutual friend as balances never exceed 3k either way except for a few times when I owed him more and just sent him a check. 

Ok to the crux of this.  I have been steady this year up about 20 units (2K) until recently.  I have been on a tear.  I am not sharing this to gloat I just am nervous he is going to skip on me and what do I have to fall back on.  The last 2 weeks I finished up 7400 total of which I have been paid 5k.  This week I am already up 5k (yes I know this could change).  My question is how do I approach this so that I get paid.  He once about three years ago knocked 2k off my balance I owed do I reciprocate?  Again young professional just engaged as of last week - some money is better than no money.  

Next question is I am leery of the online stuff but is there anyone who could legitimately tell me which way to go with that stuff.  I have been hot and honestly I don't see the train slowing down although I know it always does.  I want to max this run and lay low for the winter months as that isn't my spot.  

Sincerely everyone thanks for your time and insight.  If you want to leave jackass comments feel free but I am trying to treat this forum as what is intended for.

Best of luck!

Get paid as much as you can, and send the money offshore.  Two books I would recommend are 5dimes and bookmaker.

You will have people coming on here saying they dont like one or the other for various - mostly anecdotal reasons.  But both pay, and for a player of your size you would never need to worry about ever getting paid again.

Your situation sounds inevitable that you are going to get screwed at some point with your local.  Why not bet online with reduced juice??  I never understand this.  Unless you need the credit (which it sounds like you dont), then online is the place to be.

 Approach this 5k just as you would if it was any regular payoff.He hasn't flew on you yet and he never has flown before.A good local is better then a Vegas sportsbook and way better then off-shore.I've used all3. Don't recipprocate unless he brings it up and he may ask about a plan but is it possible that 5k isn't that big a lump for a real bookie? 5k to the guy I use is SOP. you worry alot...

I'd definitely recommend signing up with an offshore book as VANSACK suggested. You can't bet those big numbers using credit. It ALWAYS comes back to bite you in the azz and with a new bride, you and she just don't need that kind of pressure. 

In the future you should be betting 10% of the amounts you're currently at. You're begging for a life changing experience. One that's not going to be fun. 

Buy your fiancé something nice. 

Next time you are home I'd recommend meeting the bookie himself.  Makes a world of difference actually meeting the guy you are dealing with rather than going through the mutual friend.  Also decreases the chance he'll actually stiff you.