Estimating is both art & science and FWIW most professional estimators rarely get it spot on, usually operating within a Delta.There's tons of estimating books, software etc.

It would be tricky to track billable hours accurately but I’m sure there is software to make it easier. 

Most softwares will list (at least) name of guest, stay dates, ADR, and revenue to owner.

E&O insurance, MLS fees, electronic lockbox fees, association dues, contract fees, every software agents use.Many of these fees could be close to doubling by the end of 2026.

Going forward it would be good to specify that your property management software is the only acceptable method of payment in your lease (if not done so already).It might also be a good idea to check the pre-existing lease to see if they have any clause like that (sounds like you already did that).

I've been working in software consulting services for over 15 years and it's kind of disheartening that I haven't been able to figure it out, but I've got other things to worry about (like how to get a few more properties so i don't have to worry about buggie tech crap anymore :) ).

May consider software until then.

I am a Software Developer during the day, so I created a few programs for myself to just transfer some of my data into different spreadsheets from my accounts.

What softwares are you using?

Here are a few tools that I think might help you streamline your processes:I’d recommend checking out Bryt Software if you’re looking for something tailored to loan servicing.