I am in close proximity to the moment, where I will need to migrate from my old ssd and data hdd to new ones (wear and age), so I'm rethinking my environment. Please, give me suggestions about what should be improved regarding security and backups.
Consider environment as described:
In everyday use, I use Win7 (possibly upgrading to Win10 with new install) with KeePass2 (related to work). I use strong password and key file.
The KeePass password database together with key file (and 10+ dummy key files) and some other private files, are stored inside TrueCrypt volume, that I manually unlock after system boot.
I want to backup this TrueCrypt volume and make it available from my workplace too. I have chosen to use less popular cloud storage service (SpiderOak) to store that volume (instead of flash-drive, to be able to access passwords while away from PC or while unable to access KeePass\TrueCrypt compatible device). The problem is - that volume is always (PC has 95% uptime) mounted (can't copy/sync file in use resulting in rare opportunities to backup) and when I make any changes to contents (password database), TrueCrypt volume timestamp and size is not updated.
Because I could not solve this issue, I have postponed it as better solution is required. As I require access to the latest password storage from my workplace too, I use Remote Desktop connection (with custom port) to home and use my work PC as a terminal.
For connections to home PC, I do not use VPN (YET - I'm learning to create a l2tp with ipsec VPN server on our mikrotik router, but yet, to no avail), so I guess, I could have been already sniffed and I hope I will manage to solve this issue in future.
How should I change my behavior or environment, to make it more secure and backups would actually work?
PS: What security holes do you see in my current environment, that I should fix ASAP until my new environment is ready?