On insurance side of things, there is a lot of variables.

Selling for $380k means an $80k taxable gain at long-term capital gains rates (0%, 15%, or 20%, depending on income).The $80k HELOC used for personal debts doesn’t affect your taxes.A 1031 exchange could defer taxes, but you’d need to reinvest in another investment property, not a home for your mom.

on the HML did U not get a first position mortgage or deed of trust with lenders Alta ?

Their rates are good but boy, they looked at my financials and ask some funny questions such as asking for proof that I could withdraw funds from my SEP IRA account, and that I need to provide documentation to verify that  this employer sponsored retirement account allows for funds to be withdrawn, or if withdrawals could only be made in connection with the borrowers employment termination, retirement or death etc. everyday they sent me something new to answer.

I really wanted to try finding a duplex that i could immediately rent out the lower half rather then buy a SFH and have a higher mortgage overallHow did you find this deal and how did you negotiate it?

It gives you a list of all the assumable mortgages in your area.  

Hedgefunds, large buyers, mortgage companies etc. 

I'm struggling a little bit on deciding the best agreement to make sure I can get some cash flow, payback the HELOC, and not drive the new mortgage up too much with the Refi out of the HELOC.

That's three months of mortgage and utilities, the cost of flooring, and the cost of painting.

The tax paid from your lending proceeds should be the equivalent of your tax rate I would think.