As an ex-freelancer, you're trying to do too much & don't have the credibility I'd want to turn over my business to your system. I have my own systems in place - my own website, my own contracts, etc. so why would I want to use yours? Will they be relevant to my market?
It's like looking at a cable TV lineup where I might want 1 channel but have to subscribe to a bunch of others. $29 was a lot of money to me for a SaaS as a freelancer, where some months were lean and I tried to keep expenses as low as possible.
The "Personal assistant" that will answer chat queries seems like something that would be worth $29 on it's own. Is the PA a human or a bot? I'd definitely be interested in a 24/7 message taking service that could answer simple questions about my service set (and escalate more complex inquiries) for $29/mo. It sucked to have to answer my phone or get an email from a potential client when I was on-site with another client. Generic office answering services were expensive and didn't work well with freelancer setups.
I'd at least look at segmenting your pricing model - have a "Rolls Royce" option (human PA, custom responses, etc) to make $29/mo seem like the cheap option, and a starter plan I can start with, remove the risk of signing up (30 day free trial?), allow me to choose which features I want to sign up for.
Also for the first 100 or so users, you won't find them through random web signups - you'll find them in person, where you can talk to them and figure out what they really want. You don't have a product that solves a market problem right now, you have a hypothesis.