Here's  a unique situation I'd love some help on.  Let me know what you think!

A property (3,000sqft.3/2) has been on the market for about 5 months that I personally love.  It sits on 5 acres and has a 2 bedroom/1 bath house as well that has been rented out to the same tenant for the last 15 years (longer than the current owners have been there).  The rent has never been changed, unfortunately, and sits at $500/month (currently month to month contract).

Here's what I would like to do.  I have a big family and would love a few acres for the kiddos to explore.  Because of the way the land is configured, I could see myself adding another house or 2 (or duplexes?) on the property over the next several years.  I would need to bring the current tenants rent up to 2019 but would probably do that over 2 or 3 years time.

I could sell my current house @ approx. $110k, and take the approx. $54k profit (after paying off the mortgage) and roll that into the buying of this new property.  That plus the rent from the 2/1 would help pay for the mortgage of the new place.

OR

I could rent my current place out, but it would not cash flow and with expenses and capex would actually lose money for a little while.  I have approximately 7 years left till its free and clear.

OR

I could refinance my current place, then rent it out.  Because of a smaller mortgage payment, I would cash flow approximately $200-$300/ month.

Man this is a long post.  If you made it to the end and still have energy to give me some advice... big thanks.