Real Estate, Portfolio, or Pay Down Debt?

[John Dersoe]

Ok, the time has finally come. Retired.. in my late 40's. Pension of 8k per month, no other income. Closed on the house in NY, moved to Tampa. Proceeds from the sale left over total about 300k, which includes me setting aside some $$ for cap gains. So, the 300k would pay off the new house AND the 6 year new car payment COMPLETELY, total of over 2100 per month. Of course, my financial advisor says to put it all into the portfolio and if I need the $$ monthly, I can draw 2k per month as a "payment" to myself. I'm thinking "won't I get killed in taxes on that?".. So, a real estate investor says "300k could get you a cash flowing property that could make just as much or more than 2k per month after expenses".. I'm thinking.. "yeah, but then I have to be a landlord and have a cash reserve for problems and vacancies".. what do you guys think? My idea is a hybrid.. pay off the house, the car and take 50k and buy ONE townhouse somewhere that I can make a few hundred after expenses.. maybe and Airbnb or something. Thanks for any advice. BTW, it's hot in Florida!