Hey @Christopher Rodriguez
Local agent here! There is a lot to breakdown from your post and I certainly won't be able to hit it all here. We have seen the market shift some and are starting to see more of the sellers concessions in the areas surround Nashville such as Hendersonville, Gallatin, Madison, etc. However this is not happening so much in Nashville as it is still incredibly expensive and desireable.
It sounds like a great option for you would be to talk to some additional lenders/agents and get their take on it. I am not a lender, but I can't imagine you getting a $250k loan with downpayment assitance and have it be less than $1400/mo.
Buying a primary home is a great way to get into a property with little down. Also this market is a great area to invest in and has seen a lot of appreciation. So I would definitely say getting into a property if you can comfortably do so is the best option. The sooner the better!
I do specialize in all of middle TN so let me know if you would like to connect and we could get a little more in depth.