It attracts a rough tenant pool.

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

Your rental pool is higher renting out at $1000.  

Here once you start passing $1500 in rent your pool is getting pretty shallow. 

If fully updated, market rents could be 5K a month plus utilities etc.The office space is currently being used as a medical office and it's a block from the hospital so there is always a good pool of rental candidates. 

I quickly learned that pools are expensive to maintain, but they’re also a major draw for guests.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Top searches at our beach place is pool, then pet-friendly, then water view, then water front.

@Joel OhYou REALLY need to find a new pool guy.

Pool your resources (your $100k with what they can contribute).