One thing to consider is whether a two-family twproperty might provide better cash flow than a condo, especially with NYC’s high costs.

@Philip AndersonMultifamily properties in Ventura can perform well due to the area's high rent demand, but inventory can be tight.

I prefer Section 8 tenants to low income cash paying tenants but there is a damn good reason why many landlords won't put voucher holders in high end properties.

They bought it and held it, come hell or high water.

I would highly recommend a mentor or even paying a coach to get started.

But 1) you're likely grandfathered in if they ever do, and 2) there are no talks or indications of changing directions on their stance. 3) long term rentals don't cashflow here, but our appreciation is super high.

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.

Specifically, Texas has some of the highest insurance and property taxes in the nation, but the appreciation makes up for those high costs in the long run.

I can highly recommend @Wale Lawal!  

My 17-year-old daughter is still in high school, but she saved up $20,000 in 14 months as a waitress in a town of 10,000.