You sell when it fits with your original business plan (targeted NOI is reached, timeline is reached, etc.). 3.

I'd start by refining your search criteria, researching the surrounding markets, and comparing them to what best fits your needs, etc. 

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This is who will approve or deny your plans when you apply for a permit.

The plan is to use the proceeds from this rental to buy another rental property for about $650-700K, plus to pay off the home that they live in now ($260K owed).

A knowledgeable real estate agent and property manager with local market expertise can help you navigate neighborhood dynamics, connect you with contractors, and even identify off-market deals that fit your strategy.

If local options aren't a fit, expand your search to other markets with strong rental demand.

Eventually I realized that you really just need to look for a deal that fits your criteria.

If this doesnt fit with your goals, it's time to bring on a partner.

My family actually have some properties in FL, and I have also researched this area quite a bit and I saw it might fit my strategies.