The challenge we now face is whether to keep targeting smaller multifamily properties due to the historically low interest rates and very favorable loan terms or look for smaller commercial (roughly 10+ unit multifamily) properties even though the financing is not as favorable (at maximum will need to refinancing by end of year 10) and cap rates are extremely low? 

I talked about the same scenario (refinancing conventional from VA to reuse benefit) over here.

If rates DO come down in the future you can consider refinancing, but don't forget there are costs associated with that as well.

If the pricewould have been $20k less I would have been good with just a VA loan.So depending if you're looking at a larger more expensive house, I wouldn't refi the 1st one as I'm sure your interest rate is pretty low, plus adding closing cost would add more $ being refinanced.

Let's be real: He claims that he can fix an apartment building and get it refinanced to cash out investors in 12 months to 18 months.

In other words, sufficient capital for the cash purchase of a property (plus rehab) and eventually refinancing the completed project to a long term loan.

Currently only 335k left on the loan but the property at the time of refinancing appraised for about 550k.Are there any options for them to utilize equity maybe or some type of loan program that would put a lien on the property to get the issue fixed?

Speak with lenders to learn about the conditions and criteria of refinancing.

2nd home mortgage at 8.625%, will be refinancing end of this year or early next year.

Currently, the rental income would not cover the mortgage payments, but I'm considering refinancing if interest rates decrease (possibly conventional to free up VA entitlement) as well as adding a fifth bedroom to increase rental income.My Plans: I intend to retain the NC property due to a stable tenant with a recently renewed year-long lease.