What's really going on

You have two deal flows feeding each other — investing finds deals, DSCR brokering funds them. That's not a CRM problem yet; it's a shared-pipeline problem. Hiring 3-5 ISAs makes it one. The moment a second person touches a lead, ownership, next step, and last contact have to live somewhere everyone sees. And LOIs and PSAs going out by email means you need templates with merge fields, not a $80/seat suite.

What to do instead

1. HubSpot Free CRM (free, unlimited users) — build two pipelines (Acquisitions, DSCR). Free covers you and 5 ISAs on shared ownership. Watch the Sales Hub upsell — stay on free until you actually hit a wall.
2. Documint or Portant with Google Docs (check current pricing) — LOI and PSA templates with merge fields from your CRM, emailed as PDFs. This is the piece Pipedrive was charging you $80/seat for. Buy it standalone for ~$20-40/mo total, not per seat.
3. Habit: one ISA scorecard, updated Friday — dials, contacts, appointments set, LOIs sent, contracts. Per person. If you cannot see this weekly, hiring 5 ISAs will bleed you.

First action, 30 minutes: open HubSpot free, create two pipelines with stages (New Lead → Contacted → Offer Analysis → LOI Sent → Under Contract → Closed). Import your last 20 leads. Do it before you hire anyone.

What you're being oversold

Pipedrive at $80/seat is their Power tier — you'd need Professional at most, and even that's per-seat pain at 5 ISAs ($300+/mo before docs). Follow Up Boss is built for retail agents chasing MLS buyer leads, not investor acquisitions and DSCR brokering — wrong shape. And nobody at your stage needs Apollo or Outreach. Doing nothing costs you the next ISA hire: without shared pipeline visibility, deals get double-called, LOIs get lost, and sellers ghost — you feel it as "my ISAs aren't producing" when the real problem is no system.

When to revisit this

When two ISAs are closing deals and HubSpot free's reporting stops answering "who's actually producing?" — then look at Sales Hub Starter, not before.

The part worth getting right

The one call: are Acquisitions and DSCR truly two pipelines, or one pipeline with two stages? If most acquisition deals get brokered to your DSCR arm, it's one flow — build it as one long pipeline and your ISAs can see the whole lifecycle. If DSCR also serves outside investors who never touched your acquisition side, it's two separate pipelines with a handoff stage between them. Get this wrong now and in six months you're paying a consultant to untangle a HubSpot rebuild — or worse, migrating off it. What percentage of your DSCR deals come from outside your own acquisitions?