This is interesting. I'm about 8 years into serious shooting, and I wish I had laid out a detailed plan when I began. The biggest mistake I'd correct if I could would be getting training sooner. I waited 3 years to take a basic pistol course and I definitely wasted a few thousand rounds of ammo with bad reps during that time. I could definitely compress my experiences into a 5 year plan, along with some good ole 20/20 hindsight as far as gear goes. I live 5 mins from a range that hosts training courses regularly, so travel & lodging are not concerns.
Year 1: $2,109
Buy a pistol that is big enough to learn fundamentals, well suited for concealed carry, and capable of being used in a home defense capacity. Also buy ammo and attend at least 1 training course. Plan to shoot all the ammo and supplement with lots of dry fire practice.
Glock 19.5 $559 at Brownells
Send the pistol to Agency Arms for an AOS + Holosun 507C bundle + Ameriglo Suppressor sights $550 (with 5% discount code)
1k 9mm: $600
Sage Dynamics 2 day defensive pistol/red dot course: $400
Year 2: $2,129
Purchase a solid, basic carbine, basic but solid light, and 1k ammo. Plan to shoot half the ammo (zero sights, learn bare bones basics) and save the rest. Will practice reloads and stoppage clearance at home, along with regular pistol dryfire practice.
SOLGW M4 Patrol Rifle 13.7" Midgas $1,269
--comes with FSB & rear MBUS
1k 5.56: $750
Surefire G2X Tactical $70
BCM 1" MLOK flashlight mount $40
500 rounds of 5.56 leftover
Year 3: $2,244
Upgrade some stuff, stock up on ammo. Plan to shoot half of the new ammo and save the rest.
1k 9mm $600
1k 5.56 $750
Trijicon MRO + Scalarworks LEAP mount $519
5x Magpul Gen M2 30 round PMAGS: ~$75
Surefire X300U $300
500 rounds of 9mm leftover
1k rounds of 5.56 leftover (500 year 3 + 500 from year 2)
Year 4: $1,901
Rifle Upgrades + Training Course. Also practice with remaining 9mm.
Blue Force Gear Vickers Sling + Magpul QD + Magpul QDM + Magpul QD sling attachment: $62 + 20 + 30 + 20 = $132
1k 5.56 $750
Basic Carbine Course: $600
Cloud Defensive REIN micro: $359 (they typically run a 15-20% off sale at least once per year but I'll list the full price)
3 Glock 19 magazines: ~$60
Year 5: $2,550
By the final year I'd have a solid EDC pistol and a solid HD carbine, plus a good grasp on fundamentals. I'd have a decent bit of extra money from the first 4 years, and I'd use it to buy ammo & a couple training courses. Preferably FoF, perhaps with a focus on vehicle and/or low light.
1k 9mm $600
1k 5.56 $750
2 day pistol course (vehicle defense): $600
2 day carbine course (low light/HD): $600
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I'd end up with $67 to spare, plus somewhere around 1k 5.56 ball to practice with. Knowing prices fluctuate (and rarely for the benefit of the consumer) I probably wouldn't realistically have a budget surplus. I'm also the type to buy a G18 mag or D60 along the way... However, from the perspective of a thought exercise this would give me a well-rounded base of skills to build upon, I'd have a thorough understanding of my gear, and solid equipment that would hopefully last me a long time. I'd have 6 magazines apiece for the pistol and the carbine.
I chose Cowan for pistol training because I have personal experience taking his course, and 2 days with him improved my RDS pistol shooting tremendously. For the rest of the training I kept it vague because my local range hosts a variety of trainers, and there's no way to know who's going to be available in a given year. That said, I'd be looking for a "basics" course for carbine anyway (i.e. loading, reloading, moving, basic shooting positions, offsets/holds, etc.). There's a number of good instructors who pass through and could teach those skills.
Not factoring in holster/belt/defense ammo made this much easier than it would be in real life. Idk if it's "cheating" that I planned my training courses around the idea that I'd train locally, but it certainly helps cut down on costs. I actually discovered the range thanks to P&S! At any rate, the two times I traveled to Valor Ridge for training I camped in a national park that had hot showers. I'm young and I don't need a bed in order to get a good night's rest. I think it was like $26/night plus the cost of fuel. WELL below $150/night but not an insignificant cost either.