About a month ago my wife told me that she would love to have a vacation home somewhere by the water where we can build life long memories with our 3 children.

How you organize it (app, spreadsheet, paper, memory?)

He would be the executor on various properties and many of them get dilapidated as people age, move into hospice, memory care , etc.  

., as everyone has selective memory.

As doors increase, most owners shift to a single intake method for maintenance, even if everything else still feels informal.What people often move toward:Tenants send maintenance through a portal or dedicated email, not personal textsEach request creates a trackable work order with photos, timestamps, and notesVendor updates and invoices stay tied to that same threadThis setup solves the common breakdowns: missed messages, no paper trail, and forgotten follow-ups.Many small landlords make the switch around 5–10 units — not just from volume, but because memory stops being a reliable system and disputes get more costly. 

The return is lower, but they have a great track record.

What’s Neal saying now about return of capital?

Regular returns every month. 

He's getting infinite return on his /usr/bin/bash investment while you're staring at 0k trapped equity and a 5% annual return that doesn't exist in year 1 anyway.Here's the deal: Take a 65/35 split in your favor until your equity is fully returned to you (not a preferred return that "accrues" -- actually returned).

You’re returned to the beginning, not where you were.