I agree that DealCheck (or the BP calculator) does not provide enough tools or functionality to analyze those types of transactions (yet).But I would argue that it does a great job at analyzing more traditional buy & hold SFRs and multi-families, as well as flips and rehab projects. 

By a professional estimate I mean having a contractor bid the work, not just me estimating the jobs. 

Credit, jobs, income, age, married, plans for future all this matters.

As long as you focus on areas with strong job growth and analyze the deal carefully, I think you will be in great shape. 

It’s super important you prioritize the end product: something that gets the job done well as an STR.  

I'm an investor here in Columbus OH myself and have seen the city's solid and steady growth with strong economic fundamentals driving the market like major companies moving here (Meta, Intel, Google, Amazon, etc), job growth, and population growth.

The potential liability from having someone do a job they are not licensed to do far outweighs the cost-benefit.

I'm a 30 year old husband and soon-to-be dad in a dead end sales job in Alabama.

Over the past 6 months I've had one of my staff members a has done a fantastic job of building out a website and we have detailed every single property with  professional pictures and all our financials.

Jobs are always a good indicator of growth areas especially good high paying jobs.