All your help would be great, thanks!

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Is Aasha old enought to start doing that type of activity?
In moderation, yes - all of my dogs have started agility training as puppies (under 4 months) but everything is done on a 'puppy level'. My 11 month old can do a table, has a 75% understanding of how to do the Aframe, teeter and dogwalk (all are lowered in position) can do tunnels and chutes, understands how to find a weave pole entrance**, and has done some VERY low jumping chutes.
**Weave poles are very hard on young, square, upright Boxer bodies and IMO require the most consideration** (They are tough on adult Boxer bodies for that matter)
Should I get him a trainer to teach him or teach him myself?
You need a trainer to teach
you. Teaching a dog to do the equipment goes quickly, but most of the challenge to agility happens in-between obstacles. You need someone who can teach you how to direct the dog around the course, to monitor your progress, to analyze your handling, and make suggestions. I now very VERY few people who can do that successfully without a trainer - I've been competing in agility for over 5 years, I run in the excellent classes, and I STILL need someone to watch me run and handle my dogs and coach me.
Is agility a costly activity to do?
It can be, depending on how involved you get and how resourceful you are. I'm the Agility "chair" for my club, and have access to equipment and building use at no charge, and I assist the instructor I hired in beginners classes in exchange for reduced prices in the competition class. I'm also responsible for monthly "run-thrus" where I set a course and people come to the club and pay money to run their dogs.
Otherwise, classes would cost me about $15 lesson per dog per week, private are $30-60 an hour going up to $150 an hour if you train with a "big name".
The flip side is that I have to make the time to do all that...
Showing again is as expensive as you want it to be - I show mainly in AKC so entries are typically $35 per dog per day (for 2 classes, standard and jumpers) . I usually spend $60-$100 in gas to drive to a show over a weekend, and hotels can run $50-$75 a night ( I stay in CHEAP rooms ).
Also, I need to bring crates, duffel bags full of misc. training stuff, mats, treats, energy replenishers for the dogs, toys, water bowls, mats, tents for outdoor shows, special "tuggy" leashes (ok not necessary but very fun) so there's some set up cost involved when you start showing.
Overall, running 2 dogs a trial weekend runs me a minimum of $200 running 1 dog, probably $125.