Inside of the fuel tank looks pretty good to me.
As far as the cranking to get running- you probably crank a little longer than what I like to, when its not starting. Extended crank will get the starter hot (hard on starters), I like to count/crank to about only a 15 count at most. Then I stop for at least as long, as I was cranking for, or even longer.
When its cold, the crank and then waiting a little bit, will let the heat from the previous cranking, start to warm up the engine. Then crank again for a little bit. You may need to invest in a good charger or battery cables, if it sits for a long time between uses. You are disconnecting the battery switch, or pulling the cables off when you aren't there?
The smoking before start, just looks like a older engine start up in cold weather.
If you want to make your cold start up's easier, you're going to have to have a block heater and a generator (if you don't have electricity), or tarp it up and portable heaters under it. That's for under 20's, in the teens starting.
If you see colder than 0, then you're going to have also go into blended fuels and such- but I think you said you aren't planning on using it when really cold.
I didn't think the start up was bad at all. Its not going to be like a car, and running on the second or third revolution. Just had to work the air out of the system, and get rolling.
And did you check the antifreeze for freeze protection? Just a good practice every fall before it gets cold.