With the massive increase in STR properties in the US, I am hopeful that lenders and appraisers will evolve to apply income/exp metrics to STR deals specifically, on top of generic property comps.

3) What specifically do you mean about needing cashflow proceeds in 2 years?

I know that's vague but it's hard to be more specific on questions like this. 

Quote from @Emily Gowen: I only recommend investors sell when they can move the money to a better-performing investment or when the sale moves them closer to a specific goal.

DSCR loans are a great option for investors looking to scale their portfolio as they are property specific and allow you to close in an LLC

However, having an experienced real estate agent or investor in your network analyze comps adds an extra layer of confidence.If you’re focusing on specific markets and ever want to discuss analyzing deals or strategies, feel free to connect, Our firm would love to help you! 

This is going to be an issue with the majority of commercial lenders, not specific to Kiavi.

would love to see a seller finance specific calculator that has a option for 1031 exchange from buyer bringing in down payment.  

Curious how this will play out in the courts (granted it's LTR) and affect pricing products used for STR such as PriceLabs (which I use but have to seriously manually adjust for very specific reasons).

There should always be timeline contingencies factored into each projects specifics.