You need to compare your cost of living, and overall personal cashflow each money with your current situation vs. this potential new acquisition.

( I know there are certain rules to the 1031 and having 3 separate sales may be a little challenging) Also,  I thought about just refinancing the 3 properties, but the rates are a little high to cashflow well.  

Prices are high and with Hawaii STR taxes it's a lot tougher than first glance.

With interest rates being so high, I'm kind of stuck in my primary residence, unless I REALLY want to stretch things to only get into a slightly bigger home. 

High cash flow high value add Lessons learned?

So far I haven't had any issues with these tenants - they're either high income earners or long term tenants who take care of the units.

Ensure the DSCR calculations work with the high LTV and your credit score, especially if the lender won't use MTR or STR income.Lender Criteria: Some lenders won't work with new operators, some only use market rent, and others will use STR estimates or income statements from property managers with similar properties.I hop the bullet points make it easier to understand.

Especially if the CPA/firm is working on a (high) flat fixed rate.

That's kind of hard to stomach, and that in itself could be the cost of another SFH in my area.I also just despise paying high interest in general, so admittedly part of my reason for considering paying down the new mortgage is for peace of mind.

Getting a mortgage without a job will be near impossible without going with an alternative loan product that will come with a high down payment and high interest, which is not the "househacking" way.