Almost ready to rumble

indeed the awesome frogs already delivered all my stuff. So I spent the evening yesterday to go shopping in the Minmatar tradehub of Hek. I bought new rigs for some of my ships and other stuff that was left behind (sold) in LGK.
James shall have an Oneiros and a Scimitar (CTA fit) in our deployment station, Trebron should have a Naga, Tornado and 2 Hurricanes in the deployment station.
For my home system I prepared a Bomber for James and a Cynabal, Deimos, Proteus, Daredevil and some T1 frigs and cruisers for Trebron.
This took the better part of the evening to do. But some EVE time was left, so I decided to start bringing the CTA ships to the deployment station. This requires about 6 jumps through lowsec and nullsecurity space. I formed fleet with James and we headed out in a Naga and a Scimitar.
On the second outgate we landed on a Curse and two other ships(?) and I immediately knew that I was in trouble. The Naga was not really fit for solo combat, it's a specialised CTA ship. Does not even have a point. To make things worse, the large shield extender was offline, because my clone had no powergrid implant (currently training advanced weapon upgrade 5).
Two of the pirates forced me though the gate, where on the other side (of course) 2 more were waiting, the Curse also followed. To my surprise both my ships managed to warp clear before tackle could land, just to land on a Tengu on the outgate.
To make a long story short: one jump out from the Nullsec gate, where I probably would have been safe, my luck ran out and the Naga got tackled. James was in warp though. I briefly thought about bringing James back, because my opponent were only a Curse and a dps ship. But 2 seconds later a Maelstrom battleship landed on me and I decided to safe at least the Scimitar.
I gave the Naga the command to align back to the gate and turned on the MWD. I only was disrupted and webbed but not scrammed. Then I switched to James to jump him out into Nullsec.
When refocusing on Trebron I noticed that the align back to gate command somehow did not make it to the server (I hate how that sometimes happens) and I was still 18km from the gate, with shields failing. All that was left to do was getting the pod out, which I managed.
140 million down the drain.
What could I have done better? Several things:

• travel fit the Naga or solo combat fit it. Have a plan beforehand.
• not warp on like a fool from gate to gate when chased. Safe up somewhere or at least try.
• Make sure your commands got through to the server.
• Not bring two CTA ships at once. Use 1 cloaky scout and 1 deployment ship. Takes double the time but is safer.

Could better preparation have prevented the loss? Probably. I underestimated the danger and I was tired of doing hauling, fitting and stuff. I wanted to get it done finally. And I paid for it. Cocky, lazy, dead....
On a sidenote: I really really hate deploying ships that are not really solo combat fit manually. How are you guys without carriers doing it? Or do all 0.0 peeps have carriers? As soon as AWU5 is finished I will start on it again...need to make serious ISK first though. I have not much left (now 140 mill less even...must get new Naga...)