Flying with an instructor is a good idea, but let's face it: it will make us more experienced, with no influence on our "luck bag".
On the other hand, it is also a bit silly from me to ask to be lucky. We are lucky when we aren't well prepared, yet we managed to get ourselves and the plane back home in one piece, undamaged. Flying on the long run is not sustainable on luck alone, that bag will run out eventually. The only way to preserve as much as possible is using the luck factor as little as possible (by learning and preparing better and better).
When it comes to chewing capacity, this is what I try to order
and this is what the weather serves instead! Of course I have problems to chew those beasts.
At the root of the whole problem I find that renting planes to fly in the vinicity of the home base has a certain level of costs, but as soon as I want to fly longer distances (say > 140 NM), these costs will increase exponentially, not linearly. This is because the more interesting and longer trips are more likely to run into a greater degree of weather variation, so turn-backs, diversion to alternates, delays and extended opening hours for night arrivals become more and more likely with VFR-only capabilities.
In this situation, I can only foresee 3 alternatives for continuing cross-country flying safely (all require throwing a lot of ore money at flying, of course):
1) Buy a plane and become a freelancer or pensioner = I can easily wait for the tiny number of days when my next planned route is perfect VFR
2) Continue to rent, but do IFR traing and rent higher capability IFR planes for IFR flying, at least en-route = I can go into and above the clouds
3) Continue to rent, but move to another far-away country with more sun and dry air = more VFR days per month.
This is hard to swallow too, but that's the issue behind all of my (near) screw-ups.