What should I do with my primary residence?

[Theresa Merkel]

I am 40 and I own a home in SW Florida. I will have owned this current home for 5 years next month. If I put it on the market as of today, I’d probably walk away with $60,000-$70,000.

My current mortgage is 30 year 4% fixed with my principal & interest payment is $937.87 plus PMI $127.68 = $1065.55

A refinance would put me at a 20 year 2.6% principal and interest $980.90 still with a PMI but much less and would drop off quickly.

My taxes for 2020 were $2064.74 and my insurance was $2300. However, I believe I would need commercial insurance to turn it into a rental and I do not know the cost of that.

My boyfriend also owns a home.

He has paid his home off.

We are ready to cohabitate but I want to make the best financial decision for the LONG term both for us as a couple but for myself in my future retirement life as well. If I could have this eventually make me income.

Is my house worth me keeping as a rental? Long term seasonal rentals seem to do well here, charging around $2,500 a month. Possible Air BnB? Better off traditional renting with good tenants, I’d have to charge $1700 a month just to cover the cost of keeping the home.

Do I sell my home and put whatever I make from the sale in savings/investments/retirement and save some for a future together home while we live in his house for 1-2 years adding to that savings. Then we would rent his house out to help pay our new mortgage.

Do we keep my house, refinance to a 20 year with a lower interest rate and then turn my home into a rental? I believe after a refinance,

I’d have to live there another year and have to put a little bit of money into making it ready for a long term seasonal rental in Florida.

Help my 🧠 please...

What other things am I missing here?

What would be the best way for me to write this down on paper and see short term vs long term?

Part of me thinks of all I’d have to put into my home now - commercial insurance, some furniture, a RO system (I’m on well and it’s fine for me but I’d want to put that in for seasonal renters) and that makes me think 💭 nahhhh but in the LONG term that’s probably nothing?!?!

Thank you for any ideas here.