Best market & strategy for appreciate now cash flow later

[Michelle Reid]

My husband and I live in MA.  We are looking for LTR in FL.  

We have owned a multi-family in the past and got to experience ALL the pros and cons of being a landlord.  We've seen rents DEcrease, 2+ months vacancies and the joy of getting sued and selling in 2010.  So we are really trying to minimize the pain this time by getting as much info as possible.

We are looking for income in retirement.  Retirement would be about 5-8 years down the road.  We do not NEED cash flow now but would like to avoid negative cash flow over $200/month.

Our budget is around $250 - 300k.

We are trying to decide on a market.  We have narrowed down to Cape Coral, Tampa, Kissimee, Lakeland (general areas).  The theory is to find the next up and coming market with a discount to future value.  Or is that false logic?  

What market and strategy would you suggest?  Buy a LTR in a less competetive market and scale in a year or two?  Buy in a competitive market and scale?   I know appreciation is not guaranteed.

We prefer the markets with industry rather than solely tourism for the LTR appeal.

Thanks for reading!