How many housing lotteries do I have to enter before I win?

[Pablomaldito]

I appreciate everyone's reply except that troll, you are all right it would be best to either wait till new wards are added in 6.3 or wait till the day before or morning of the last day. I was really hoping some from SE would reply with something but I probably won't get that reply lol

No, its not best to wait until new wards are added in 6.3! The strategies we were talking about were specifically for that single round when the new 6.3 wards are added. If you want to get a personal house on your server, you have to participate in every lottery round even though the chance of winning is extremely small. The launch of 6.3 will just offer you a single round where your chance of winning may be higher than 10%, but that's it. There will never be a time when you actually even have a decent chance of winning a personal house. The launch of 6.3 will just be when you have the least terrible odds of winning.

The only way to get a guaranteed house on an established server is to make a shell FC and snap up a FC house. Those remain available for a long time after the launch of new wards. Make your FC ASAP if you want to go this route, because you must be in the FC for 30 days to be eligible to bid for a house on its behalf.