(First Post) Renting our existing home to fund another?

[Anthony Thomas Winfrey]

Aloha, 

I'm wondering if anyone could offer some perspective on what you might do in our situation (or what options we might have). A situational backstory, and I will do my best to be succinct; 

My husband and I are in the process of both looking for a first home for ourselves and also helping my aging (69yr old) mother to decide what to do with her existing property, as we are planning to move her in with us following my father's passing. We (husband and I) live in Hawai'i, and he is eligible for VA loan under the disabled veteran criteria (100%). He pays no property tax in HI because of his VA status. He makes a grossed up (because tax free) income of $57k, and has no debt of any kind. Credit score is over 700.

Mom's property is 40 acres with a 4br/2ba, 1400sq ft home in Southwest Michigan, on which she still owes about 67k. We are nearing completion of the remodel on this property to either sell or rent (within the next 60 days). Her mortgage on this property is $386/month. She has something around $280k in equity in the house, on which I understand she could get a Home Equity Loan of perhaps $200k. She makes a grossed up $27K tax free income. Credit score is over 720.

We are interested in figuring out creative ways to fund our new collective property in Hawaii. We have found a couple different options that fit our needs, and we are trying to decide on a plan of action. Wondering;

1.) Could we use cash from a home equity loan on the property in MI to provide a down payment for a new place in HI, and if that could be used as a gift to us and allow us to use my husband's VA loan?

2.) Can we count the future rental income from the property in MI to qualify her for a loan on a new place if they were to instead use a non VA loan and go together as cosigners?

3.) Would it be better to simply sell the property in MI (roughly $500k, conservatively) or would it work better to rent it with a property manager? 

4.) I, myself purchased a 3 acre vacant parcel in a subdivision that I only owe maybe $16k on, and could be paid off immediately, if necessary. Would it be better to try and fund a construction on that property instead?

I feel like there are a lot of options available to make this work, but it's a lot to orchestrate and as a first time buyer, I'm looking for advice or someone who could provide some perspective for us.

Thank you for reading this, and for all the information in this forum and the media content this place provides. I greatly appreciate it!