A second opinion on your resume certainly couldn’t hurt. If money’s a concern, I think there’s a community on Reddit that allows you to submit your resume for review? Tread with caution, of course, but it could be worth a shot. Or I’ve seen people on LinkedIn or various job sites that help give back to their respective communities by providing resume feedback - I’d probably look for people in HR or who work as hiring managers.

That sucks about your business, but I think being honest about it is your best bet if/when it comes up. Businesses fail for a variety of reasons, plenty of which won’t necessarily reflect poorly on you. And if the gap is the last five years, well, there’s definitely been enough going on in that timeframe that you won’t be the only one with an employment gap.

Applying for jobs can often be a numbers game, but if you’re not reaching the interview stage at all you may want to have someone review your resume for you. It might be that you’re not highlighting your skills and experience in a way that the systems will pick up on - every industry seems to have it’s own buzzwords - or you might also have a resume format that the ATS can’t parse correctly.

I’ve been using Summit lately and like it so far; the dev is responsive and there are quite a few customization options.

I previously used Sync (now abandoned), Jerboa, and Connect as well. Jerboa didn’t seem quite so customizable, but it was a nice and simple UI.