If you work until you get the full SS benefits, there is a certain age where you can keep all of the social security check and work too in order to make some side money. Otherwise I think for every $2 dollars you earn you have to give back $1 from your social security check. You can Google this.
Not sure exactly what that age is, but they speak of FRA or full retirement age. Then you can work and still keep all of your benefits check. (as I understand it)
The more marketable skills you have that you can use while traveling, the better off you will be. Selling online, salesmanship, arts & crafts, electrical/mechanical, sewing, lite carpentry, etc
I belong to AAA and in the past I would buy Travelers Checks there at face value cost. (one of the benefits of belonging)
I have used an "free online hard drive backup" to store check numbers in case something happened to them so I could get replacements. Never had any problems, but I thought it would be a good idea.