We ended up connecting with a local insurance group, Pope Insurance Agency, here in Boston.

If you talk to someone like the folks at Wren Insurance Agency (from what I read in the Wall Street Journal), you’ll find they’ve been adapting to the shifting market conditions with some interesting coverage options.

With fresh paint throughout inside and out, brand-new roof, dual HVAC systems, updated water heater, stainless steel appliances, lighting fixtures, outlets, countertops, and PEX plumbing just to name a few.

i.e. single proper Buyer agreement, exclusive buyer agreement, etc.Does the principal broker her a signed agency disclosure with this party?

In some instances it becomes apparent I will be awarded a better contract price if the listing agent dual represents the transaction.

I've had success simply informing the tenant that I plan to involve a collections agency as a next step if they don't pay what they owe.

Is this agency legit?

First, don't use REI Reply, it's just a white-labelled/private-agency version of GoHighLevel (the actual provider of the CRM) that they just mark up and charge you extra for everything you do (every text, email, etc is 2-10x more expensive than just linking twilio/mailgun to your GHL account, etc).With that out of the way, you can get to making workflows.

Any insights into pricing trends, STR regulations, or running dual-use scenarios (STR + LTR) would be incredibly helpful! 

The agency, of course, is trying to maximize its resources, so would love to have you charge less rent.If your focus was primarily on gaining excess rent, keep in mind that there is a reason many landlords will not take vouchers.