If you have not contributed post-tax dollars into a traditional IRA, the total amount converted is taxed at your normal income tax rate and the Pro-Rata rule does not apply, but in this case you mentioned you have an IRA so I'm sure it does. 

Since you'll be living in one of the units, you can qualify for owner-occupied loans, which often have lower down payment requirements and interest rates compared to traditional investment loans​

The key is finding the areas / neighborhoods with strong rental rates that are not saturated with too many LTRs.

Between rates being higher and terms being shorter Helocs can also have issues when it comes to DTI and not having reserves. 

In this high-interest rate/high-price market, house-hacking is more about offsetting as much cost as you can.

I am currently renting at 40% below market rate rent and will be putting 5% down.

You can get higher but the rates will be higher as well and it will be a lender that doesn't sell the loan to Fannie. 

Especially with higher interest rates and also location dependent might be more geared toword appreciation. 

How has the occupancy rate been for you and Avg nightly rates? 

I've never done a dscr loan but if rates drop after your (most likely) pre-payment penalty ends, I'd refi.