Don't beat yourself up too much over the past. We've all made mistakes and I could count a lot more than a few thousand dollars I am out if I had made a few different choices. As far as making better decisions going forward, I don't personally think a financial planner is usually necessary, except for very complicated situations. In any case, I think the general consensus is that if you choose that route, find a fee-only planner, not one who makes commissions off what they recommend to you. And/or one that is a "fiduciary" so that they can only do what's in your best interest, not what maximizes their fees/commissions.
I also suggest not getting too stressed out about "getting in on a deal" as much as doing careful research about what your best options are. Yes, doing a lot of this research exposes you to people that have gotten in on deals, whether real estate, entrepreneurship, blogging, dividend investing, you name it. And probably most of us are caught between feeling like we were the unlucky/dumb ones that missed out on great opportunities, or a frenzied race to see if we too can get in on any of them. But getting anxious probably only makes us more susceptible to making poor decisions. Because I've never spent enough time to identify nor been lucky enough to stumble upon a great deal I could get it on, I've mostly gone the traditional route of index investing and trying to increase my frugality. And being happy with less than I thought I needed. Something like that is at least a good plan to start with, to find a place for that cash, while you invest your time, over a slightly longer horizon perhaps, in researching and identifying exciting deals that make sense for you.