Remember why you started this journey in the first place and focus on your long-term goals.

you want to stick to 6-24 month terms 

@Lindsey Mannix - the agent report was left pretty wide open in terms of comps in the area.

I would think about this in terms of A) prices to access the market and B) overall market growth. 

What kind of financing terms were you looking at for the remainder?

There is an amazing difference in knowledge, skill, and experience between long term agents with whom real estate is their career (life) and the agent whose in real estate because he’s a career SALESMAN selling the hottest thing; you know, the guy who’ll be selling oil well drilling participations next year, and advertising services the year after. 

I am sure she is sending him letters (or using other methods to contact him) as well.I'm a small long-term buy-and-hold investor myself, but this property is about 4 hours away from my own market, and would be used personally by my wife and I if we were to acquire it.I'd really like some help from you large operators who work these deals all the time, as to how best make contact with the owner and see if he were interested in selling.  

Investment Info:

Single-family residence buy & hold investment.

Was purchased as our primary residence, then we moved and have been renting it out.

Numbers in FL are not looking great with insurance/taxes/HOA fees/etc for cash flow but willing to  focus more on just breaking even (or close to even) and having significant long term appreciation.Option 2: take the cash, pay 20% long term capital gains and wait as market continues to dip for a prime buying opportunity.Would greatly appreciate insight/advice from those much more experienced and knowledgeable than myself.

If you were to rent it out long term, that's where you cross the line.