That person today has spent six figures and has yet to break $1M... 

So much so that you might consider breaking it up into separate posts on each subject.

I believe the one good thing about that spreadsheet is that it can be adjusted by the State you live in. because costs are different in every State the estimate sheet i believe is based on a multiplier for the corresponding State, as most cost estimating books are based. that program does break down a lot of information for you and i think it is a good program, one thing you may want to check is if the program updates every year with current multipliers for the States ( program is probably based on a starting average value for each thing and then the multiplier changes as prices for materials change) and you want to make sure it does that.

If something breaks and they're not shopping around for deals with contractors, is this the person you want to be working with? 

To highlight the basics of DD, we like to break it up into 4 areas: financials, initial walkthrough, compliance, and paid inspections/services.We like to begin with the items that require just your time, but not money.

Flexible when we needed a break from living on our boat.

Items I would like to see integrated:- CRM- Email Marketing Campaign (likely from CRM platform)- Issue/Break fix tracking

I'm able to start with my annual goals and break them down quarterly, then into monthly and weekly tasks, then down to daily habits and tasks.

So it will barely cashflow or break even. 

This should, ideally, get more cash flow, and allow you to hire a PM without breaking the bank.