They have been the best investments I've ever made, but hoping to have greater cash flow influence with a daily business model.Is there demand for these types of rentals in the investment community?

Quote from @Cathy Li: It's a white label software built on go high level.

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.

@Edward Toomey V It's unfortunate you had that experience with a software purposed for landlords; however, I'd hate for you to give up on software designed to work for landlords and ditch to QB.  

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

Can I ask you a software lead sourcing question?

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

May consider software until then.

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 :) ).