I also don't quite see it as being the same as picking a city to live in - I went through that process in choosing Austin but that was more emotionally driven. 

I've always had this dream of a beach home within walking distance to the beach, so I realize I probably need to back up and look at this more objectively instead of emotionally when it comes to extra wear and tear and higher insurance costs, weather impacts, etc.

Don’t hesitate to seek professional advice for financial planning or even emotional support if things feel too heavy.

Booking a vacation rental is an emotional decision and people will convince themselves to pay more for a place that tugs at the emotional strings.

The emotional side of me is so angry that they damaged a house I put a lot of work and TLC into, and that between damage and lost rent, basically a year of profits from the house will be wiped out, but the logical side of me thinks I may be throwing good money at bad.

I'm reading between the lines of your original post and for some reason I think there may be an emotional pull to this property.

Try and separate emotion as best as you can from the situation.

Emotions have no place in this game.That being said, if you want help on specific aspects, like lead gen, or networking, those would be good things to inquire about specifically...

If the couple is fighting, emotions will rule their actions, not common sense or financial responsibilities.

I really want to jump into it as soon as possible but I know an emotional purchase is not smart.