Keep in mind getting it to current HUD standards will still not make it qualify for traditional lending if you end goal is to sell it. 

The family selling the house had had a death.

I am looking to sell my primary home in 2025.

Now govmit this way ( west coast is going for super high density ( in your area U already have it in row houses) issue out this way is market is not receiving them I  know a few developers that built this planning department dream and they cant sell them :)

I’m torn between selling it and finding an apartment/whole building in Tokyo or doing some light renovations and testing the rental market with the older house.

There are a lot of owners I know that will sell, but these properties have value so they need 1031 purchase targets before they let them go. 

They construct and sell houses in Florida using some kind of green technology which allows a tax rebate in addition to an 18-22% APR. 

At least they’ve given up selling the LLC as asset protection but I don’t think it does much better for privacy from anyone that actually cares to find out. 

I have around 300k in a company stock account that does well with dividends, so don't really want to sell of shares.Would taking a personal loan or doing a margin loan make sense?

You could become a private lender for people who flip homes, invest in notes or tax liens/deeds, speculate a bit on buying new construction and then selling for a profit when complete, buy shares of a REIT etc.Orlando is a fantastic place to buy and hold, build new construction or even own a STR.