Too Many Questions... Too Many Ideas!

Hi!

I've been kind of forced to connect in a general Wordpress forum because I have a few different important plugins interacting on my site and I have a vision for what I want my site to look like and how I want it to function, but I'm having trouble bringing it to life.

So here's the lowdown:
I run a membership site. I charge members a monthly fee to access past and ongoing content. That part of the site is functioning fine. I'm using a combination of PaidMembershipsPro and LearnDash, which I love. I'm trying to branch out into singular course sales. What I envision is a place where people who are not members can purchase a singular course, get access to that course only (not the entire membership area) and have an easy way to transition to a full membership if they'd like, when they've finished with their course.

I'm having trouble setting up the sales of the singular course, I'm trying to use a combination of WooCommerce, and LearnDash.

I have a bunch of other ideas for things that I'd like to be able to do with my site (such as a first time login page) but I feel so lacking in knowledge that for some of these things I don't even know where to start.

I keep thinking maybe I should hire a developer to help, but I don't know where I can find someone reputable and affordable that has knowledge of all these different plugins and how they interact.

Does anyone have any suggestions or ideas for me? I'm getting frustrated by my lack of progress on my ideas and I would really appreciate some help or a new perspective!

-Jess