If you are going to self manage you will need to build business systems and get a list of reliable vendors.  

You basically sell to your self but still own it. 

The only thing that might give me pause would be if I did not have sufficient capital on a building that was older but had appeared to have significant maintenance issues when I was looking at it to buy.

Hawaiian real estate law differs from other western states significantly, mostly due to its monarchal heritage and the Bishop Trust influence.The basics are the same as would be in California; determine the condition of title ownership (individual(s), estate (including conservatorship, if appropriate) OR fiduciary acting for trust.Use a qualified private money equity lender to make a loan sufficient to buy out the cash-only beneficiaryThe legal community in HI and Big Island in particular is small.

Even when I self manage I include pm because it is work and I do not work for free.

Moreover, I would recommend prioritizing a W2 position over 1099 self-employment/sales for two reasons.

Have you considered using a self-directed IRA to invest rather than cashing it out? 

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

We are only selling completed homes with our own in house financing currently at 3.75%, a huge discount from most bank rates.We are a long time property provider for some of the bigger podcasters: Real Estate Guys Radio, Marco Santorelli (Norada), Kathy Fetke (RWN) Jason Hartman ( Empowerd Investor) GRE (Keith Weinhold), Whitecoat Investor Group and more We also work with American Homes for Rent, Invitation Homes, Crescent, Haven Realty (JP Morgan) to name a few on the institutional side We are partially owned as of 2022 by Sumitomom Forestry, which means we have no bank debt and self fund all our building projects.

Are you self managing those properties?