Ordinarily those tenant vacated damages would be too remote, but it sounds like they were contemplated by both parties at the time of contract.Were I in this situation I would be looking to state law to determine if the EMD is truly the extent of my potential liability as a buyer. 

But tell them what you are doing precisely - vacation rentals, not regular rentals.

I use Beyond pricing in my vacation rental markets and Pricelabs in my city/mid-term rental markets.

What works best really depends on your goals and risk tolerance, but here’s a quick rundown of what I’ve seen happening in the area:STRs: These are still solid in vacation-heavy areas like Naples, Fort Myers, and the barrier islands.

Think of it like the idea of wanting to go on Vacation and asking a group of a million people where you should go.

Although, I enjoy Tampa, I'm just not seeing the same opportunities. 

Remind them of quiet hours, city ordinance, right to quiet enjoyment, etc.

If you want to think about it as a math problem, it’s all about where you put your time to maximize returns while also factoring in what you enjoy doing.Picking the MarketI’m the kind of person who gets analysis paralysis.

I was definitely not going to miss the opening weekend haha.A movie is definitely more enjoyable after walking 3+ miles to see it.

Examples might include areas in the Midwest, Southeast, or Sunbelt regions.Multifamily Properties: Consider duplexes, triplexes, or small apartment buildings to increase unit count and spread risk across multiple tenants.Short-Term Rentals: If you’re comfortable with the management requirements, STRs in vacation or business travel markets can offer significantly higher cash flow potential than traditional rentals.Value-Add Properties: Look for opportunities to buy undervalued properties where you can force appreciation through renovations or better management.Decision FrameworkRun the Numbers: Compare the projected cash flow, equity growth, and tax implications of selling versus holding with a refinance or HELOC.