Personally I have not been a huge fan of Medisoft but if your familiar with it then that is a plus. Are you a billing service or a provider? With a billing service the big con of cloud based is usually price. Most cloud based softwares charge per provider or per practice. For us that isn't practical. We use Lytec which is very similar to Medisoft but in my opinion better and more user friendly. We have over 50 providers and the cost is perfect. Some of our providers we bill from their systems using their software. IMO Lytec stands up well to most systems. For us, not being cloud based has not been a problem because we use a remote login to access our system from anywhere.
Hope that helps.
Michele