Am I getting in over my head? 😬

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Hi all! I'm sorry if this is long and confusing. I am new at this. 

I own a condo in Mililani, HI, that I bought in September 2015 and currently live in. It's financed via a HELOC (popular thing here in Hawaii), and I have a decent amount of equity in it, about $150,000, with $50,000 available to use.

I am considering buying a small studio here, a leasehold for $165k (cheap for Hawaii), with a very low lease fee until 2078. I plan to move to the second place for a time (it is much closer to my current job), and rent out the first (already have a property manager lined up). I would put $16k down on the new studio using some of the equity from my condo.

Here is the complication. My job is flexible and allows me the option of working remotely. My whole family is in New Hampshire, and my dad is currently in a nuesing home with dementia, so I'd like to move closer to home for a year or so, starting later this year. I'd also like to use my VA loan to buy a home in New Hampshire, since that's where I plan to eventually live permanently. My VA loan is 100% available, and would remain so even if I bought the studio here in Hawaii.

Question - is it unwise to buy the second place in Hawaii? I want to get it mainly as a place for me to come back to for my job from time to time, but ultimately as a second rental property. However, I don't want to jeopardize my chance of being approved for a VA home loan in New Hampshire. My income is good, about $85k not including rental income, but that would be about $500k of debt hanging over me. Both places would hopefully be rented while I'm gone (for a total of about $3800k per month), and I do have an over two year history of getting rental income from my condo (I've been renting out the extra bedrooms). However, I don't want to end up in the position of having both places in Hawaii, but being unable to qualify for a $300k or so VA mortgage in New Hampshire because of the debt to income ratio.

Any advice would be greatly appreciated!