Here is a list of Construction, Rehabbing & Generic PM softwares that may be a good solution:Construction, Remodeling & House Flipping Specific PM Softwares BuilderTrend/Co-Construct - Home building project management software specifically built for custom home builders.

My recommendation is still going to be the same as I've put in other threads; buy 1.25x DSCR in a very good area or up & coming area of a very good city ideally through BRRR(you'll keep 10-30% of the capital in the deal likely), invest ideally 60-80% of your downpayment(no less than 33%) in a debt note fund that matures in 2-4 years.

I’m very big on having the proper customer support and making sure if I buy something I can contact their support to get more info/refunds etc.

"Custom woodwork with an artisanal flair."

Find one that does not have a high-priced long-term monthly contract, flexible pricing, and excellent customer service.

What should the "ideal" comprehensive check list include?

Find one that can be custom to your needs, has flexible pricing, no long-term, high-cost memberships, and excellent customer services to determine how to best market to your leads.

To expand, @Ben Whittington, Dennis Doss and Anthony Geraci’s firms can prepare a customized set of loan docs for you in any state. 

So, you have to understand your customer as well as part of learning your market. 

They want to be paid 5 figures or more but can’t be bothered to learn more than their customer.