What are your experiences with telecommuting and what is the best way to get into it?

I have telecommuted when it was necessary to support my family. I wasn't a fan because I was a supervisor and couldn't make daily, face-to-face contact with my employees. They were great and trustworthy people, but I was old-school enough to miss the personal contact.

Some of the things I did when telecommuting:
-ensure my boss and employees understood I was at work even when I was only available by phone or e-mail
-ensured the employees and my boss knew who was "second in command" if they couldn't reach me; empowered my deputy to make time-critical decisions in my absence
-used teleconference to attend meetings with my boss and his other staffers
-set up my government-provided laptop with a VPN so I could access all the files and e-mail like I was at the office (this is critical to telecommuting and one of the great uses of technology)
-checked e-mail frequently and tried to respond with the same professionalism and timeliness I would have if I was in the office
-had a short teleconference with my employees near the end of the normal duty day to ensure they were progressing on work assignments
-we didn't use electronic meeting software often because it proved to be unreliable at the time (2011-2013) and often more trouble than it was worth compared to a teleconference

I was on the Fed/MIL side when telecommuting became a "requirement". Up to that point, the dinosaurs pretty much tamped it down. First prerequisite is trust between the employee and supervisor. Second is a job that can be done from home. So we had project managers, contract specialists, engineers, environmental types, etc. do it. By the time I left, I'd say about 30% telecommuted 2-4 days a week. That allowed hot racking some desks. We also had some pretty stringent criteria for what's at home. No high speed internet, forget it. We moved telecommuters into NMCI laptops and they just used them at home with their CAC cards. They forwarded their work phone to the home number and it didn't make a difference. You really don't care where they are at so long as they pick up the phone when you call and the work is being done. We'd see an overall productivity jump as telecommuters were less bugged by walk by BS at work. Supervisors sometimes telecommute if they're locked up on some investigation, board report, etc. We had a pretty extensive ad-hoc program that provided for it.

So what holds you back? It's likely trying to be 100% sight unseen telecommuter material. People hire employees to work for them and have varying comfort levels with telecommuting. So that means a routine day or so at work for designated meetings. People don't go to your house. So take a look at your expectation level.

I am a Freelancer working mainly from home. I do make it to coffee bars to work depending on my activities for the day. I love the flexibility, and I enjoy the three big gigs that I do. All of my Telework/Freelance gigs I got through my personal networks in Anchorage. After 100+ bids through on-line freelance website I got nothing. I know it takes time to crack that code.
Some of thous websites are Freelancer.com, UpWork.com, FlexJobs. Recently I discovered and currently testing CloudPeeps.