This is something I try to live by and teach my kids if I can - "A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.

This strategy balances tax efficiency with proper estate planning.

I've come up with a plan though.

In order to do this you need to have deal flow and you need to know 1) How to recognize a good, profitable deal, 2) How to put together funds quickly to buy the deal before someone else does and in such a way where you are protected and the deal is protected, 3) How to run the project so that you follow the budget and don't overspend or overbuild, 4) How to attract an end buyer or a renter and which documents to use to protect yourself and the buyer, 5) If you are going to keep the property then you need to know how to set up the property from the start to best help you in the refinance later, and 6) You need to know how you are planning on managing the property from the beginning in order to make sure it will be profitable at the end.

I would like to start close to home as I plan to self manage the rental side of it.

Suggest you get your game plan in place first then go forward once you have the goal in sight.

I have some upcoming repairs needed that outweigh the Homestead Exemption and plan to make my primary home a long term rental in the next 7 years but the repairs can’t wait.  

Quote from @Patrick McCann: Hi Justin, I'm also a househacker in NH currently living in my duplex in Dover, NH with plans to search for my next one in the near future.

We just love the country and plan to visit often and figured why not expand our business into Japan.

The plan was to pay cash, refi out and use that to improve the property.