While they generated some cash flow, I found the effort required to manage them wasn’t worth the return.

By the 3rd or 4th year if they aren't the same or have increased we all prob will have bigger problems

(that means I work for Airbnb as an independent contractor, a paid, by Airbnb, consultant to new Hosts).Here is my "tip" that I send to new Hosts:"Pricing is key and worth doing some homework.

That may increase your cost or limit the coverage you can get.The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

I also like the sponsor, generally speaking, who is going all in with at least a third, and preferably half, of their net worth on the deal or fund.

Housing has always been super affordable there, and new construction has increased in recent years.

Before jumping into the condo, I’d take a closer look at whether the $300/month cash flow is worth it compared to other options, like a small multi-family property or a property in a higher-yield market.

Without actually building the 3rd unit, would this new triplex eligibility increase my property's value? 

How is this juice not worth the squeeze?

Waste of time, huge room for error and zero reason for a customer to do this.....any Contractor worth his salt will have better pricing/quality/selection on the big stuff and will have guys on his crew that can do those dreaded 'parts runs' for the little stuff.