I just figured it'd be worth mentioning, as a more potentially more productive (and cost effective) strategy to get the end result you are after. 

After that I post the property for sale, I call others with similar properties, and I follow up with potential buyers...

Currently, we are leasing the property, generating a net profit of $380 per month and living in Missouri.We are contemplating the decision to sell this property and potentially gain $239-278K payment to buy additional investment properties in Missouri given the rising rental rates in the area, we anticipate increasing our rent and potentially securing a net monthly profit of $780 (annual$9,360).While we acknowledge a monthly profit, our concern stems from the apprehension that the property might not fetch as high a price in the next five years or that our HOA fees and taxes could escalate.Given this situation, what course of action would you recommend?

There's a potential to use the maximum eligibility with these 2 purchases but you can House Hack them and increase the cash flow vs market rates in the area.  

See if someone sticks out as a potential partner. 

A smoking deal will consist of an asset that is severely underperforming but has clear potential (and you can prove it), or is an overlooked hotel that has the opportunity to change brands to a more upscale brand, thus increasing the rate and occupancy and becoming more valuable.

Candace@Ariella Jacques   One potential downside is that when you refi you will only be able to pull out 80% of the market value (so leaving 20% of your cash behind)  instead of having the option to put down as little as 5% when you use a loan to purchase. 

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

I have started looking into repositioning assets and trying to hit a higher NOI.A few considerations that I have been looking at are NOI, Future potential, and appreciation.Does anyone have a model they use to decide what properties to hold vs reposition?

If there are too many for the house size it can be difficult to secure financing or potentially sell the property one day