What are your biggest pet peeves about working with an agent?

This really creeps me out, despite claims that there are tons of opportunity (mostly from real estate agents).Example:List Price: $699,000Airbnb Calc: $92k/yrProperty Mgmt Est: $85-95k/yrWOW!

As Caleb said, use your experience here.Find some investor-friendly agents and wholesalers to start looking at deals.

Worse case you can furnish it and put the property on Airbnb or peer space as a venue space or STR in between long term tenants.Using an agent or property management company to at least get it rented could really set you up properly.

Most insurance agents should be able to write that policy for you.

I'd suggest networking with some of the rock star agents like @Eudith Vacio or @John Warren above to help you narrow down your search criteria. 

Maybe some specialty programs exist for prefab homes or a custom ADU builder might have his own lender partner they could refer you to... but unless you yourself are an experienced home builder with a track record in ground-up construction, you're basically looking at a hard money or a HELOC.

I would find an agent in the area that is familiar with the area and investing. 

Interview a few agents and you should get a good idea of list price and estimated closing costs.

Cities and regions experiencing economic expansion tend to attract more renters and offer better long-term investment potential.