Short vs long term rentals

[Kevin Reid]

Can anyone direct me to a good pro con list or advice article? 

So my wife and I are having a hard time deciding our direction in life. We know we want to invest in some kind of real estate in the next few years. We keep going back and forth on what to do. We don't really need the cash flow as we have decent enough careers, we are just looking to build equity to use towards a slightly earlier retirement. For context we live in Lakeland, FL.

Way We see it we have a few options.

#1 (safest) buy another home locally and rent ours out long term. We know our house, it is desirable, and know what we can get for it.

#2 (semi safe) stay in our home and add a pool. Then buy some local inexpensive property to rent long term. Again we know our area and what we can do more or less.

#3 (riskier?) Stay in our home, and use our money to get a small short term rental in a city in SW FL. We would use it for a week here and there in the slower months. This is the "get your feet wet" deal as we have no experience as landlords for STR.

#4 (riskiest?) Stay in our home and buy a nicer property, somewhere with water access in SW FL for a STR. We would still use it in slower months.

#3 & #4 worry us a bit as they are so dynamic. High and low months, cleaning......plus we have to furnish it....

Anyone have both LTR and STR? Which do you prefer? For STR do you go with a management company?