I am a proponent of buy and hold rentals. It is tough to beat those monthly checks over the life of holding rentals. However, this deal just fell into my lap. I have options: buy and hold, STR, or flip.

This deal came about starting over two years ago. I stopped and asked an owner if they wanted to sell. They declined. OVER two years later, they contacted me. I was surprised they held my info all the time.

When I went to view the property there was also another agent present. I offered cash and the other agent was suggesting a listing price higher than my cash suggested purchase price. The owner stated they did not want to list the house.

After some careful thought I realized this deal really made no sense to buy and hold. Returns would be very poor. So I decided to walk away. I again suggested to the seller to let me list the house even if for 3-4 weeks. I told them I would cancel the agreement if they brought in a buyer.

When I thought we were done I got a text from the owner. They dropped the asking price enough to make sense even doing a flip. I talked to a couple of flippers and was told they would probably give me a 10K assignment fee. Not bad for a few days work BUT....I am closing on the deal instead. 
Now the questions comes: do I rehab it and then resell or just sell it with no lipstick? I believe the profit is almost the same so my inclination is to sell it as is without the headaches of dealing with contractors.

There are NO 3/2/2 properties in Cape Coral under the high 140's and most of those are wood frame older houses. This house is built around 2004 and is CBS. My inclination is to list it at a low price and then let the bidding wars begin.

My OTHER option is to lease it to a friend that does STR. I believe he will pay a premium price, take over all maintenance, and give me a slightly better return. He just told me he wants to take over any vacancies I get and set them up for STR.

Whatever the decision I am closing on the property. I may be a flipper after all!