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.

I just bought my first rental property in Baltimore, MD, and I’m planning to rent it out by the room, including the basement.

My cost basis for my properties are consistently off from my tax returns because Stessa will include everything in the basis even though it shouldn't be.  

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

Pairing that with relationship-building will help you uncover off-market opportunities and find local experts who can guide you.For meetups, here are a few ideas:Indianapolis Real Estate Investors Association (Indy REIA): They have a mix of virtual and in-person events and are a good starting point for networking with other investors in the Indy market.Louisville Real Estate Investors Group (REIG): A similar organization for the Louisville market, with educational and networking opportunities.Check out BiggerPockets Meetups: Many cities have local meetups organized by investors active on BiggerPockets, and they often include virtual options.Facebook Groups: Look for local investing groups like "Indianapolis Real Estate Investors" or "Louisville REI."

For example, Schwab, massive changes including what I consider bonkers high interest rates.

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.

@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 coastal land is already near built out including Miami.  

Regarding the condo/townhome situation in Fort Myers vs Bonita Springs, I would say the more important things to focus on would be the association fees charged, what is included in those, and the rental restrictions of the association.