I am / was in the timber business in the NW west and sent LOTS of logs to Japan over my career.. so have a little bit of understanding.. not an expert.. plus when you say a home. in Tokyo that could be literally a 50 sq ft little box  LOL literally. 

I say as soon as you get rid of the pmi , turn your house into a rental and buy another primary residence with 5% down . you will be on your way to be a real estate investor . 

Mike when i say "a lot of cash" i should probably be more specific here.  

Note: Massachusetts is one of those rare Corrupt States that does not allow Title Companies to facilitate the Closing .I understand the whole process such as Municipal Lien doc and pro rated division of Taxes and so on and so onThe Broker is trying to say a Lawyer must be present .I say the Broker and Lawyer can simply go play with themselves , and if you want a Lawyer present, you can pay the worthless dirtbag from your own funds.Note , I have been involved in numerous Closings in the past, thou not in Massachusetts and have prepared more than one quitclaim deed in my day.Has anyone done a closing in Massachusetts without using an attorney ?

Would someone be kind enough to break down the expenses, terms, what to expect based on say a 50k loan to determine OOP expenses and profit?

Let’s say a painter at $30 an hour multiplied by eight hours equals $240 dollars a day.

I would say a car port may make sense if you're in the North East, but not sure it makes sense based on where you live.

@Michael Shires  Knowing the Waterloo market and that you're in experienced in remodeling, I would say a good investment may be buying, renovating several properties, flipping some and holding some. 

The Realtor I discussed this idea with is affiliated with said property management firm and he is quite sure he can nail down the ROI and rentability.This is contrasted with the investing opportunity in say, a small commercial building, a few residential SFDs, or the like. 

Compare that to say a 200k house and 1400–1600 rent locally off the mls here in Raleigh.