Buying STR with current rates as a retirement plan?

[Kiko Mattoso]

Hi everyone,

I want an honest answer about something. I own only one STR property upstate NY that gives me around 11% cash on cash return. This means, I get like around 10k per year, net. But reading some posts here on Biggerpockets, this deal will sound bad to a lot of investors who say they only consider deals that can generate at least 20%.

My long-term goal is to buy enough STR properties that will generate a cash flow of 20k/month, so I can retire in the next 15 years with live with this cash-flow money.

BUT, in NY the homes are expensive and with current interests rates, I am not sure now buying STR properties is the way to go. I probably can get 10% investing in stocks. Not sure I wanna go that route, though.

My thoughts: I could buy another house now that would generate another 10% Cash on Cash return, and get around 700 dollars per month in cash flow, but then I'd have to buy 25 properties to reach those 20k. I'd need to buy 2 per year, to achieve that, but I don't have the time or money to do that.  

I know some of you will say " find better deals, maybe not in NY" but how when you're on a 9 to 5 job?

Any advice? What is the best free tool to help me find the deals? I love real estate, so would prefer to find ways to make it right, than to invest in stocks.

Thanks a lot in advance!