Why

Five reps splitting New York and New England, one inside SDR, and 10–50 inquiries/month is exactly the shape HubSpot Sales Hub and Pipedrive were designed for. The wishlist tells me the real problem: your current CRM isn't capturing email and call activity automatically, so nothing downstream (stale-account alerts, weekly reports, opportunity suggestions) can work. That's a data-capture problem, not an AI problem — fix capture first and 80% of the wishlist falls out for free.

What you actually need

1. HubSpot Sales Hub Starter ($20/seat/mo) or Professional ($100/seat/mo) — Starter gives you the email integration with auto-logged contacts, mobile app for adding accounts/opps on the road, and basic sequences. Professional unlocks the "no contact in 6 months" workflows and weekly rep reports you described. At 6 seats, Starter is $120/mo — start there.
2. HubSpot's Gmail/Outlook extension + mobile app — installed on every rep's laptop and phone. This is the single feature that makes auto-contact-add and email monitoring actually function. Without it, no CRM on earth gives you what you're asking for.
3. A habit — Friday 4pm pipeline standup (30 min) — your inside SDR runs it, walks each rep through accounts with no activity in 60+ days. The CRM surfaces the list; humans decide kill or chase.

Do this today

Sign up at hubspot.com for the free tier, connect your own Gmail/Outlook via Settings → Integrations → Email Integrations, then install the HubSpot Sales extension in your browser. Send one email to a prospect and watch the contact auto-create with the thread logged. That 10-minute test tells you whether HubSpot's capture actually works against your real email before you migrate five reps onto it.

What to ignore

Skip Salesforce Sales Cloud ($165/user/mo) — it's built for 20+ rep orgs with admins, and you'll spend six months configuring it. Ignore anyone pitching you Apollo, ZoomInfo, Outreach, or Salesloft on top of the CRM; at 10–50 inquiries/month with warm referral flow, you don't have an outbound-volume problem those tools solve. And turn down every "AI co-pilot" add-on until your basic activity capture works — AI on empty data is just an expensive guess.

What doing nothing costs you

A conservative 15% slippage on 30 inquiries/month across 5 reps = ~4-5 lost opportunities. On capital equipment (molding/extrusion lines run $100K–$500K+), even one missed follow-up that closes elsewhere is a six-figure year.

Where this leaves you

You've got the tool choice (HubSpot Starter, upgrade to Pro when the 6-month workflow matters) and the capture-first sequence. The plan configures the NY vs. New England territory views, schedules the rollout so your inside SDR migrates first and trains the four outside reps one at a time, and names the week-two moment when one rep "forgets" to use the mobile app and the whole capture loop breaks.

When to revisit this

When auto-captured email activity is logging cleanly for 60 days and you're ready to turn on the 6-month dormant-account workflow.