As for picking a specific market - I would go after one with an increasing job and population growth.

However, the rapid influx of new residents, coupled with insufficient housing inventory, has driven prices skyward, making homeownership increasingly unattainable for many.

I would also like to refinance an STR to either increase cash flow or potentially cash out to buy another property. 

I've already done quite a bit of research in my area and can already pretty much tell you what a property is worth or at least generally what it will sell for as I spend about 3 hours a day looking at properties and have been doing that for about a year to make sure I'm prepared on the accuracy side of things.I do have a family member that is a real estate agent in the area, but I'm not sure if a standard single family residential agent is the correct connection for multifamily.

Our primary residence along with our vacation home is worth about $1.4 million, have a million in stocks etc.. credit score is 700+  How the heck do we get qualified for a loan? 

Then ask why the property tax rates for hotels on Maui hasn't increased in over two years, yet they continue to raise it for STR's as well as non-owner occupied residential properties.

If you intend to have it managed after purchasing, reach out to a couple STR property managers and have them offer their perspective on what's worth fixing, what amenities you need, and how much they would rent it for.

I’m closely monitoring a few tenants as we speak. 1 requested to pay this Friday after payday due to a job change. 1 is $200 behind from last month. 1 got a rent increase but still has this month at the previous rate.

It's worth 50% more than I initially invested and I've pulled out all of my capital via cash flow.

If you don't have a lot of experience cold calling or managing a team, I would recommend using one of the companies that already have a training program, they will hire and manage the VA's for you for a small per hour fee, well worth it.