I don't know where to begin investing into my site

I've been blogging for over a decade and in the last 4-5 years have made a small amount of money. I still work fulltime and recently started a family and am looking at investing what I've made back into the site. But here's the problem. I have no idea how to go about hiring someone, what "job" I'm even looking for, and have had trust issues with fiverrr work in the past

I probably need to just get over the trust issues. But even then I still don't really know what to do. I've done everything for my site but had no formal training in most of it. Writing, editing, photography, seo, wordpress, webhosting, etc... my site feels more like a Frankenstein website that is running by sheer willpower.

I'm sure I have optimizing that I'm not aware of; I know I have emails leading to digital sponsorships, I've done alright with affiliates etc. and think all of these are jobs I could hire out. But I don't know if I just write a bunch of small gigs on something like fiverr for email answering, various SEO work, keyword research and optimizing, etc. Or am I looking for a single person, maybe an assistant editor that I pay part-time for XX hours per week?

I have some other ideas for hiring a social media person or an editor to help me publish a book and have a physical item to sell which feels should happen before I spend any $$$ on marketing

I get a few dozen contacts for some kind of collaboration most months. It takes more time to email back and forth coming to an agreement than actually doing the "work" on the site. I feel like this is proof of profitability to me and I could streamline my end by hiring someone to help make the deals.

But what does that mean? Do I go on fiverr again? Do I need to come up with an hourly work flow and make a part time posting somewhere like Indeed?

Sorry if this ended up rambling or totally in the wrong sub. I just know that a little extra help and expertise right now would go a long way and have the cash to hire someone right now.