Assuming you're not a developer yourself, how do you (not)handle certain issues that arise? What issues hit you the hardest?
For me, it's keeping the team motivated and inspired on Tribe of Five (www.tribefive.me).
We're past the honeymoon phase when everything was fun and new. And now we're in the "oh man, there is going to be lots of work" phase. And that requires someone to keep the team motivated and inspired and looking ahead.
Miss-communication from both sides
Communication, I work in a different state than my developer and find it hard to consistantly communicate with them. I started using Trello for certain things which has helped.
Trello is a great resource! What specifically do you use it for?
I have used it for work order processing. It is easy to comment, critique and set due dates on certain edits that need to be made.
Not a developer, but I hire freelancers to help build the project. For me, the biggest struggle is reaching out to them once the main project is complete. For example, when a bug appears or an update is needed it can be difficult to get their help again. Usually they have moved on to a bigger job or no longer use the freelance website, etc.
I've found freelancers incentives to be at odds. Their goal is to wrap up a project and move on.
Your goal is to make your product awesome. And no matter how much you test...as soon as the product hits the market, you'll realize there are tweaks / iterations / changes that need to be made.
Longer term, are you still planning to stick with freelancers? Or is this a short term bandage?
Yeah, it can be hard to keep freelancers motivated or feeling invested long term.
I have had 2 small projects with freelancers. For my current project I still have one good freelancer on board and I am considering learning the necessary skills (with help from friends) to fill in the gaps.
You need to get them on a retainer
How does that normally work? Like a contract with a monthly fee?
I do a project for you. You pay me $10k. After the project is finished you agree to pay me $500 every month. For that money you get 1 day of my time every month. If you don't use it you still pay but at least you know you get me for a day if you need me. You can also use that to get teh dev to do security updates, reindexing of db, performance tuning etc