Indecision! Sell both houses or sell one and rent one?

[Karen R.]

I'm in a quandry and just cannot decide what to do. I have a family property with 2 houses on 5 acres in Florida but I now live in Pa. I am retired and need a monthly income but renting so far away from where I live gives me considerable doubt. 

House #1 is 1000 sq ft and is a fixer upper, it sits on 2.35 acres. It needs work. House #2 is 1800 plus sq ft, 3/2 with inground pool and detached garage, sits on 2.5 acres. It needs "lipstick". 

I have received dozens of offers on House #1 from "we buy any house" people. I have not replied to any of them... yet. This is the house visible from the road. House #2 is not visible from the road and has a different address so buyers don't know there are 2 houses on the property. Each house has a separate deed, so can be sold separately, but I think I'd prefer to sell them together. Or not. 

So here is my dilema:

I NEED a monthly income. I would prefer to own property closer to where I live in Pa. but the rental would not be as much as Florida. Yet,if you add in the cost of travelling to Fl,paying for property management, etc.,I don't know if there is an advantage to Fl. 

My options are: 

• A straight up real estate trade, Fl property to Pa property
• Sell house #1 and use the funds to add "lipstick" to house #2
• Sell house #2 after adding "lipstick"
• Rent house #2 after adding "lipstick"
• Sell both houses "as is" then find a duplex close to me in Pa

Any and all suggestions are welcomed. Right now there is a "caretaker" living in house #2 who was supposed to be rehabbing house #1 and I've found out he hasn't done anything of the kind! I'm tired of being ripped off,so I need to fix this problem. Thanks for your input