You should be able to get a good spotter & tripod for well under $2k, especially if you buy used.
A used Swaro ATS or STS should run around $1400, a decent tripod about $300.
The Gen 1 Razors are $899, tripod $300.
The Gen 2 Razors have slightly better glass (imo), but I preferred the dual focus...
Stating a budget would help us provide better recommendations.
For the money, the Vortex Razor is hard to beat. Not lightweight, but it doesn't sound like you'll be packing it around. For your stated usage, I'd go with the 20-60x85 1st Gen.
Kowa, Swarovski, Leica make very nice spotters, but...
Had a Decked drawer system and thought it was very good, but my dog crates wouldn't fit with the cap on. Using totes now ( I normally don't carry that much stuff), but may add a bed slide at some point.
I've had Snugtops, Leer, and ARE. Of the 3, I'd rank ARE as the best quality, then Leer, then Snugtop. I think Leer owns Snugtop now.
Never had any major issues with any of them, but the Snug top always seemed to need something retightend.
Never had a cargo management system, but one of the...
Are you anywhere near St. Louis? Frank, the owner of Zykansafe, Zykansafe.com, really knows his stuff. He's a member of SIGforum and is generous about helping others make good decisions.
Nothing wrong with a college education, but I sure wouldn't go deep into debt for it. A wise man (my father) once advised to always be able to make a living with your mind in case your body gives out. I got a BS Degree in Business Administration and worked in various management and...