Launch · small landlords · Chicago HQ
Deploy before the portfolio outruns you
Missed deposits, rent in personal accounts, and Sunday maintenance texts do not scale past a handful of doors.
Start with Deposit Desk and banking at 1–10 doors · add ledger and light PM at 10–20 · automate at 20–40.
Not endorsements · compare plans yourself. Not legal or tax advice.
1–10 doors · rough tier
Headaches: missed deposit deadlines, no move-in paper trail, rent mixed with personal cash, “I’ll remember” maintenance.
| Job | Deploy on launch | Why |
|---|---|---|
| Deposit compliance | Deposit Desk · Pro for print + .ics | 765 ILCS 715/. Chicago RLTO itemization |
| Banking | Separate business checking | Clean deposit return + audit trail |
| Files | Google Drive folder per unit (lease, packet PDF, photos) | Disputes need dates |
| Calendar | Deposit Desk · Google Calendar one-click + .ics · Sheets CSV | Surrender date drives 30/45 days |
| Screening | Per-lease service (e.g. SmartMove, RentSpree) | One bad tenant > tool cost |
| Insurance | Landlord policy · liability limits reviewed | Not optional |
| Rent | Check · ACH · Zelle with written ledger | Spreadsheet OK here |
| Maintenance | Shared notes or text thread + photos | Upgrade at 10+ doors |
10–20 doors · systems tier
Headaches: inconsistent move-in/out, lost vendor receipts, tax prep scramble, who handles Sunday leaks.
| Job | Put in place | Why |
|---|---|---|
| Deposit + deadlines | Deposit Desk Pro · email reminders | Same IL rules · more turns |
| Rent ledger | Wave, QuickBooks Simple Start, or Stessa | One source for income + expenses |
| Light PM | RentRedi, TenantCloud, or Baselane | Rent + maintenance without enterprise bloat |
| Leases | eSign (Dropbox Sign, DocuSign) | Versioned addenda |
| Maintenance | Operator logs or PM ticket module | Pattern before crisis |
| Ops doc | One-page SOP: move-in, move-out, late rent | Train helper or spouse |
| Tax prep | Tag vendors in ledger monthly | 1099 season |
20–40 doors · automation tier
Headaches: owner reporting, autopay failures, vendor SLA, compliance at volume · spreadsheets break.
| Job | Start automating | Why |
|---|---|---|
| Rent collection | Autopay via PM (Baselane, DoorLoop, Buildium tier) | Chasing rent does not scale |
| Accounting | Stessa or QB + bank feed · monthly close | Partner or bookkeeper ready |
| Maintenance | PM tickets · optional Latchel / Property Meld | Dispatch + history |
| Screening | PM-integrated pipeline | Same criteria every lease |
| Deposits (IL) | Keep Deposit Desk if PM deposit export is weak on itemization | Statute timing is not “PM default” |
| People | Part-time bookkeeper or VA · clear roles | Software ≠ staff replacement |
Deposit Desk fits where
- Pro today: up to 40 units on one subscription · built for operators through the automation tier.
- 10–40 doors: many teams still use a focused IL packet tool beside PM software.
Records only · not legal advice. Confirm IL rules with counsel.