I only recommend using a HELOC for scenarios where you'd be able to pay it back within a year.Alternatively, you can just buy another investment property with lower down payment, which is a better interest rate than anything you'll get on a 2nd lien HELOC/HELOAN. 

What I have found is that right around 2-4 properties, most people are tapped out on DTI and are unable to qualify using a conventional loan. 

For some background info I just closed on my first home using a VA loan .

If there is anyone who is using a trust to transfer mortgages to their LLC, I would love to shadow and learn more.

Tenants save money when using a shared meter, so there's plenty of room for error when calculating how to distribute the charges.

The 2nd question is should we pursue the investment property even though we are more cash strapped than normal due to the remodel and if so, would using a HELOC make sense? 

So you can go ahead by that first house with FHA and then buy the second one using a conventional mortgage. don't worry so much about the second property yet. 

That I could take some of my inheritance and savings, around $400K total tied up in investments with TD Waterhouse, and using a portion of it to invest in a rental property(s)Currently without a job and hesitant to return to a similar situation, I'm at a crossroads.

I understand they are using a promissory note, But have you thought about getting some kind of legal opinion before getting involved with that option.

Have you looked into using a local credit union for financing?