I’m not looking to be the GC (obv) on this and will be hiring a GC.  

They will be able to guide you in the right direction and tell you if your project is feasible or not.From there, we hire outside consultants to take the plan through the approval process.

so even though I enjoy coaching, I can only justify doing it if the income from the coaching justifies hiring someone else to do another one of my responsibilities.

Reciprocity is key to building lasting relationships.As you look to expand into short-term rentals (STRs), research the market thoroughly, understand local regulations, and consider whether you want to handle property management yourself or hire a professional.Remember, growing a real estate portfolio takes time and persistence.

I wouldn’t do the work myself, but hire a contractor.

@Alesha Walker, a tradesman who wants to be hired for an expensive job has a vested interest in up-selling you on something that may not be your best option.

Here are the five reasons serious (particularly luxury & commercial) investors should hire an investor focused and friendly real estate broker: - Market Insight: Seasoned investors will show you why the little things make a big difference.

If they don't, hire an attorney. 

So, for those who frequently hire contractors (good ones), how do you find good contractors?

I'm not aware of software that automates this since a lot of the numbers being input are assumptions made by the analyzer.I will tell you you can dial in your processes around analyzing deals and hire someone to run your processes within your buy box.