The property is currently in an LLC that is a disregarded entity that flows to another LLC taxed as S-Corp. 

This is as much to keep accounting and taxes easy as it is anything else.

I first got introduced to Tax Lien/Deed investing about 2 years ago, I've bought a couple books to further my knowledge and while they have been very insightful, I feel like I'm stuck at this one spot; getting started, or making that first investment.

Do I have to have a lawyer for closing since this is a vacant lot?

I have used the same property manager the entire hold and have had zero issues and extremely happy with management, tenant placement and help on property tax reduction.

Or in other words, the rent received from house hacking would cover our housing costs (mortgage, property tax, insurance, repairs, utilities).Upon research however Oahu seem to be a high cost and low cap rate area similar to SF where we currently live.

They're like real estate taxes. 

They handle payments, payoffs, and year-end tax information. 

Unlock financial peace with Rapid Fast Cash! Trusted for years, we specialize in expert tax consulting and services, including swift tax refund assistance. Our year-round availability ensures tailored solutions for ba...

How do I get my money back with minimal tax liability?