The "problem" is old age. 
My tag says it all - I'm 70 yo and don't learn as quickly as I used to. That makes taking on IL-2's bewildering collection of workarounds very time consuming. If someone could provide a step-by-step procedure without the usual ambiguities I might give it a try, as I do have a copy of IL-2 1946 laying around someplace.
Old age is no bar Geezer, 70 is just the time to start enjoying yourself especially as I would think you are certainly now retired from what the day
job was and able to utilise your free time for the best things in life.

The game itself does not actually need to be complex from a modding point of view, it depends on what you feel you want to add.

Once you have a game that is up to date and equipped so you can actually add things to it you can have your input as simple or hard as you feel ready for.
The aircraft and their complicated lods and dead models are top of the scale both in 3D terms and if you wish to do java work, however, there can be a huge difference in complexity between the WWI types and the jets.
The objects of yours are at the easier end as far as actually getting them into the game once you have done the 3D, no issues there for you.
Obviously if you want to do moving vehicles and have them shoot at things it gets a little more involved, but if you just wanted to add your objects in the way I have then I can certainly take you through that, you would just need the relevant tools applicable to your 3D programme, primarily here those that can afford it use 3dsmax and others like me make do with gmax.
As far as getting your game to the modded state from the IL-2 1946 disk all that is usually available at M4T and here, only issue is download time because there are a few years worth.

You will find the mod activators here and all the help you might need to add them.
Best bet I think would be to get yourself a working version first and see if it floats your boat and if so move on to using the mods first, that way you can just enjoy every body elses hard work and let them do all the stress.
Anyway, I have now added the buildings to the download thread so we here can all enjoy your hard work.

Take care of yourself.
Wishing you all the very best, Pete.
