However, some amenities consistently deliver high value because they attract more bookings, increase nightly rates, or result in better guest reviews.

I have to pressure them to take care of it. 

Most agency loans will expressly forbid such an arrangement, so if they found out, the odds of having the loan called would be very high. 

They also benefit from strong schools, which can be a huge draw for long-term tenants.While you may not achieve high cash flow immediately in these areas, the property values and rents tend to appreciate steadily over time, aligning well with your goals.

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.

. - The people that are monetized on actually closing deals are all saying this thing is highly implausible. 

After 5 months we had a bad water leak under the house.

I would highly recommend moving your tenants to a PM software where you can screen tenants, collect rent, etc. 

Generally, homes closer to the water are more expensive.  

Option 2 is high risk, as financing may be tough on your situation.