I vintage or casual blazer over your bear-o-dactyl t-shirt and jeans will have the desired effect without making you look like a suit. You can also easily take it off or put it on depending on who you are dealing with over the course of the day.

Agreed. Agile really was designed for frontend applications where the majority of the work is in the user interface. Games, web sites, iPhone apps are great candidates for Agile/Scrum. But I would never Scrum a prison door controller or a missile guidance package. Some things you have to get right once or not at all. Secondarily, Agile is not a one-size-fits-all. A consultant cannot set up the process for an existing team. Every company takes the form and modifies it to produce better outcomes. Sure the book-Agile is bad, but I love the Agile we run in my shop.

1. Contracting: Assuming you are in the states, be prepared to give 30-40% of your earnings back to the government. As a self-employed person, you get taxed twice, once as business income, and then again as personal income. This is why contractors typically charge $80-120/hr. They only take home $50-72. Also, don't expect our "business friendly" government to help you out in the insurance department either. If you can qualify, you may be looking at $1000+/mo to insure your family.

On top of all that nonsense, you still have to find work, and it's unlikely to be steady. You may have a huge flood of work, and have the opportunity to work 60-70/hr weeks and make a huge payday, or just as likely, you may have to float yourself for 3 months on what you've saved up. Your best bet here is to get into a software niche and build up a loyal staff. This will not only provide steadier income, but also allow you to hand pick people that you enjoy working with.

2. If you get along with people and have leadership skill, then yes. You should know by now whether people tend to take their lead from you or not.

3. An MBA is a great way to network with other people who are aiming towards executive-level positions. This will pay off in 3-5 years as some of those people land those positions and you can ride their coat-tails, or they can ride yours if you are the lucky one.

4. I'll let others take a crack at that.

KeePass satisfies all of your criteria:

• Open Source: It uses an OSI-certified license.
• Multi-user: You can throw the database on a Samba, NFS, etc. share and it will merge changes between different users that have the DB open at the same time.
• Secure: Supports multi-factor authentication.
• Linux-based: Works with Mono.

If you are using iPads, besides enabling parental controls, you might also want to prevent access to the home button. I've seen this done at a few well put together installations. A few pieces of plexi-glass and some silicone adhesive will do the trick. If you use some other opaque framing material, you can even make it look like you paid many more thousands of dollars for custom technology.

Make sure you have a compelling narrative in your cover letter about why you left the field and why you want to come back to it and stay in the field for the long haul. I tend to overlook gaps in skill and employment if the person Im hiring won't waste my training investment and they have a background that is complimentary to the team I'm building.