WH living is not for everyone, but it can be a lot of fun if you have a decent group. You really need to understand the mechanics as well as the strategies involved in WH PvP, especially WH defense and assaults (as you won't last long in WH space without that knowledge). You can ease yourself in with some of the smaller types of WH's (C1's, and C2's), but there usually isn't a lot of money to be made in them unless you do manufacturing, PI, and mine (but PI can make quite a lot of money as the planets are as good as null sec).
With that said, security of gear is an issue. You don't have a station that has separate areas for ships and equipment for everyone, you only have POS's. Which means if you don't have individual POS's, you are at risk of thieves unless you trust everyone living in that particular POS (or has roles to open/use those particular tabs).
For the smaller WH's, you can usually get good defense simply by bringing blueprints and building several ships that are too large to physically fit through the entrances/exits of the wormhole, specifically several POS bashing ships, like domi's, or a dred or two if you really think you are going to stay there for a while. It is hard to take out a couple spider tanked domi's when the biggest thing you can bring in is a crusier (the only things that will be a real threat will be a T3 fleet, but even those will be cautious because the combined drones for 4-5 domi's will do one hell of a number against any T3 fleet, even one with logistics since you can also fit some heavy neuts on those domi's as well to neut out any cruiser in seconds).
You also absolutely need to learn how to D-Scan, which is a skill not many learn (even most null-sec guys don't do use it as often as they should and simply rely on local to tell them that a blob just jumped into system). The strategic use of bubbles can and will save your countless times.