It defies logic that the lender would not have a firm date by which they must be repaid.

Yes, if you do end up converting a primary home to a rental property the insurance carrier must be notified of the change as it's a completely different policy with different coverages.It's not a difficult change to do but if you don't make the change and a loss was to happen a claim could be denied.

I'm a new investor whose been listening, watching, and trying my best to get a start on this awesome journey.

It all comes down to an investor's goals and what they are trying to accomplish.

Even looking at the balanced rate (which I feel like is hard because the terms are different) along with the potential to have the monthly payment/fees covered, it feels like a cash out is a better option if we did want to keep this.Part of the current struggle is that the market was hit harder from the rate increase so sales are almost at a standstill and even with trying to sell the house, the rental market is doing substantially better because most military cannot afford to purchase in this area as the payments are over 6k/mo for buying vs 3-4k/mo for renting.Any advice is most appreciated!

You should have something in the promissory note about a prepayment penalty.Still, there must be some other issue going on here.

If you go the 1031 route, here are some rules when trying to combine multiple sales:1. 

It must be private or hard money lending, or cash from your own resources.But, while you can't take title to the new property you can have it under contract before you close the sale of your old property. 

You can sell that property as the trust and buy as yourself or as a "disregarded LLC"(an LLC that you are the only member of and that also does not file it's own tax return.In a 1031 exchange, the taxpayer for the old property must be the tax payer for the new property. 

Try http://www.outbounders.com/