The first apartments I rented as the owner, were previously rented by the former owner at $150 month including utilities. 

That’s because it can include renting furniture and decor to more fully transform a space.How Do I Know Which One To Pick?

Down payment of $13K including reserves sounds pretty low to me . ( Based on Maryland )

HOA is currently $172/month, with and additional $44 for club fees, covering club amenities, including a gym, boat lift, a restaurant etc. 

This would include adding another bedroom and making it a full 2 bath.

STR insurance provides broader coverage, including liability, property damage (even non-guest-related), and gaps Aircover might not cover.For damages caused by guests, document everything (photos, receipts, estimates) and file a claim through Airbnb.

Or the listing agent includes it in the property info on their website, or shares it when a showing is scheduled.

@Pat Aboukhaled I would ULS (unit lot segment) the primary house and include a clause in the call option that would prevent them acquiring the DADU.

THE VISION: With 130 units and 8 buildings plus a wedding and event venue, our vision includes revamping this space into a dream hotel.

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.