Hold vs Rent Old and Buy New

[Eric VanGrinsven]

Hey everyone. I'm a bit of a newbie in the real estate investing world but have been a fan of bigger pockets for some time. I wanted to see if anyone may have suggestions for me based on my current situation. First a little background:

I'm a 32 year old Nashville native and purchased my first home here back in October of 2014, a 3 bedroom 2 bathroom 1275 square foot ranch. I was a little cash poor after the down payment so I immediately dove into house hacking and had renters in my 2 additional bedrooms before Thanksgiving. I continued house hacking for several years and was able to get the house paid off in exactly 6 years to the day(October 29,2020). I made a lot of big payments toward the principal balance over those years and in retrospect could have put those savings toward a down payment on another property. I've followed Dave Ramsey for years and liked the challenge of paying off the mortgage as soon as possible. 

Fast forward to today and I continue to house hack with one renter. I've saved up a pretty good bit in non retirement savings and am now looking to possibly deploy those savings toward a new property. The only problem is Nashville's housing market is white hot so houses are not only expensive but also get scooped up quickly. This market is really unusual and I don't really see any end in sight to the continued growth of the city. I guess my question could go in a few different directions: 

Do I deploy those savings toward a new house and rent out my current home using that cash to pay down the mortgage on the new house? Or do I use that same tactic to pay down the mortgage on the new house to the point where I can sell the old house and use those proceeds to pay off the new one?

Or do I just continue my simple house hack, save the money, and see if the market levels or declines and jump in then?