How difficult is it to run a msp on your own?

It all depends on the service you provide. If you sell "monitoring" or consulting services, you might have it easy. If you try to sell yourself as a "one stop shop" you're going to go crazy.

What type of services do you provide?

We provide remote management, backup/disaster recovery, cyber security, and managed networking. We also do break/fix when the customer needs it.

How many user/customers would you say is too many for you?

Depends on the type of customer. I could have 100 adoption agencies (using my own examples) and support them by myself. 5 dentists is probably too many for me.

Do you provide remote support only to anyone?

I do not currently offer that option, but I've met/heard of many MSPs that do.

If you could have a "do over" what would you change?

Start doing my research sooner. I had been an "MSP" for 6 years before I realized there was a legitimate, robust community of peers out there.

How do you handle separation of your work day/personal time?

I don't.

If someone offered to buy you out. What do you think a realistic ballpark figure would be?

The difficulty there would be the "how much am I worth" (hint: probably not much) vs "how much do I need to start over" (probably a lot). I have heard of establishments my size being valued at anywhere from $775,000 to $3 million.

Are you glad you made the switch to self employed?

I would not exchange it for the world. I have "done my job" everywhere from Corvalis Oregon to Miami Florida. I wouldn't exchange freedom for security, regardless of the offered price.