It’s wild how something as simple as file management becomes the hardest part of the process. You’d think in 2024 we’d have this figured out, but here we are, renaming PDFs like it’s our side hustle.
That line hits way too close to home. I’ve had deals where I spent more time tracking down which version of a document I sent than actually analyzing the property. The spreadsheet idea is smart—I do something similar, but I’m always second-guessing if it’s worth the extra effort. Sometimes I wonder if there’s a better way to “prove” you sent something, or if it’s just inevitable that underwriters will ask for the same thing three times.
Curious—have you ever had an underwriter push back on zipped files? I’ve had one or two claim they can’t open them due to “security policies,” which just adds another layer of fun. At this point, I’m half tempted to print everything and mail a binder, just to see if that would actually speed things up.
Also, do you ever worry about sending sensitive info over email? I get a little paranoid about bank statements floating around in someone’s inbox. I’ve tried password-protecting PDFs, but then they’ll say they can’t open those either... It’s like there’s no winning.
I keep thinking there must be some secure portal or tool that actually works for both sides, but every lender seems stuck in their own system—or lack thereof. Is there any tech solution you’ve found that actually sticks, or is it just spreadsheets and renamed files forever?
Honestly, I’ve lost count of how many times I’ve had to resend the same doc because “it didn’t come through” or “the attachment was too big.” Zipped files are a gamble—half the time they bounce back or someone claims IT won’t let them open it. I tried using Dropbox links for a while, but then you get the “our firewall blocks that” excuse. At this point, I just keep everything in a folder on my desktop called “Lender Chaos” and hope for the best. As for sensitive info... yeah, it’s nerve-wracking. Password-protected PDFs seem like a good idea until someone can’t figure out how to open them and you’re stuck walking them through it over the phone. If there’s a perfect system out there, I haven’t found it yet.
At this point, I just keep everything in a folder on my desktop called “Lender Chaos” and hope for the best.
Honestly, that’s way too relatable. I’ve wasted hours chasing down docs that “never arrived.” Here’s the thing—if you’re dealing with lenders who can’t handle basic file sharing, it’s a red flag for me. I started using Google Drive (with expiring links) and just tell them up front: this is how I send stuff, take it or leave it. If their IT can’t handle it, maybe they’re not worth the hassle. Time is money.
I get where you’re coming from, but I’ve actually had a few lenders who flat-out refused Google Drive links—said their compliance teams wouldn’t allow it. Kind of annoying, but I guess some of them are just stuck in their ways. Ever tried DocuSign Rooms or something similar? That’s worked for me when Google Drive was a no-go. Curious if anyone else’s run into that...
Yeah, I’ve run into that too. I thought Google Drive was pretty standard, but apparently not for everyone. One lender straight-up told me they only take email attachments—felt like I was faxing documents in the ‘90s or something. It’s frustrating, but you’re not alone. DocuSign Rooms worked for me once, but even then, there were weird hiccups with their system. Guess it’s just part of the DSCR loan circus... hang in there, it gets easier once you know what each lender wants.
