I worked with a gentleman named Jarom there. 

There are times and seasons for everything!

However, after doing this I discovered there's a 6 month "seasoning period."

You want to see something that has low or no seasoning for a cash out refi.What is your draw fee & benchmarks for the repairs portion of the borrowed money?

That will give you an idea of what expenses for the place are during all 4 seasons of the year.

@Patrick Britton it can be all over the place and also depends on the kind of property...i.e. is it seasonal, business travelers, big city etc. 

Also plan on a 6 - 12 month seasoning on the property before most banks will refi your cash out.

I’m writing to find out from seasoned investors about there opinion.

You need time to save up, time to season the loans, and time to pay down the first while you move on to the second, time for rents to increase and for loans to pay down.Here are a few strategies:Moving is one strategy.

You can find an older Honda or something similar that's reliable and that you can afford with no car payment, and then use the extra money that you were paying on this car's monthly payment to pay down some of your other debt.Unfortunately you're in a bad position with the more expensive car because you can't afford to keep it but you also can't afford to sell it since you're so far upside down on the loan right now.But I'd do whatever I could to start chipping away at some of that other debt.