At this stage in my life, these equity plays are more impactful than holding onto a property for a couple hundred dollars of monthly cash flow.What’s your take?

The committees have never said they'll require a specific form of evidence to show that you've rented the place for at least a couple of nights.

I have sold a couple of businesses as well, and speaking from experience, you are never more vulnerable to make a mistake than when you are sitting on a giant pile of cash.Also, I agree with @Corey Conklin - I'm a big fan of "overflow cities/towns" in the sun belt.

I have integrated a couple of other platforms and had to do the exact same steps when it came to being able to receive payments online.

If you are single or a couple on the same page about house hacking, look for uneven multis.

No way to say for sure since each lender is different and I have no idea of the terms you need or your FICO, but it is typically the prime rate plus a couple of points.

I'd personally sell the townhouse (doesn't sound like it cashflows or would make a good rental property) - you may have no capital gains if you have lived in it the past 2 out of 5 years - I believe the first 250k for single filers is exempt from taxes and the first 500k for married couples.

Waikiki area (however there are a couple STR buildings outside Waikiki), Turtle Bay (North Shore), Ko'olina (Westside) and Cottages at Mauna'olu Estates.  

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

My firm has several lenders who can seamlessly close in 15 days on 'traditional' mortgages at/below market rates and we've been doing so for a couple of years now.