I track all my finances in Quicken on a desktop PC with Windows 7. I enter all my receipts and then download the transactions in a web connect file that imports into Quicken to make sure I don't miss anything and to reconcile. It's a great system for keeping exact track of all my finances. It's secure because I use a wired network at home and am meticulous about protecting myself against malware. All my passwords are secure, etc. However, I'm moving and will be sending the desktop across country with the movers. I'm taking time off work, about three weeks, to drive across the country. I'll have Quicken with a laptop. At hotels I'll be able to access the Internet with my laptop via wifi. Will it be safe for me to go to my bank's web site, pull up my accounts, and download the web connect file? Or is that too risky? I could just meticulously enter the receipts into Quicken and wait until I'm in my new home before accessing my bank records. I could just use the hotel wifi for general non-sensitive web surfing. Btw, I'm using Kapersky Internet Security.
As long as you are using ssl encryption you can send private and sensitive information without worry. Check you websites that you send these information to and make sure their connections are secure by looking for an "https" and not a "http" Like "100" says, If for any reason your connection is interrupted your still in the clear with ssl, all information is sent with security packets. All your login passwords and account information is encrypted with ssl just be sure you check the websites certificate. ssl is in a sort a form of a VPN if someone attempts to intercept you information all they will get is a garbled mess, and the server will send a new encryption packet key that only applies to your connection with the server.