@Marc Shin, I echo Gino's thoughts.First the financial: assessing any improvements will come down to how those improvements affect both your cashflow and your overall value of the asset.  

I also was clear Jonathan is not a friend or even an acquaintance and you repeating it does not change that fact.  

If you can build equity and pull out cash through a BRRRR (Buy, Rehab, Rent, Refinance, Repeat) strategy, that could get you the funds you need for that larger down payment on a multi-family or HUD loan.

Focus on the Buy, Rehab, Rent, Refinance, Repeat (BRRRR) strategy to build capital through flips and value-add properties.

He does not need another source of income, especially not one that might negatively affect his supposed source of wealth.If you truly believe he is trying to help, then what is his track record of helping?

I dont want to cash-out refinance because my margins are very thin already and refinancing to a higher rate will only increase my monthly payments and negatively affect cashflow.

Occasionally, someone who hasn't used credit much is disproportionately affected by very minor negative things on their credit report.

If your hoping for repeat guests (where they pay full rate and you don’t have to share it with Airbnb or VRBO), then provide hotel size shampoo, conditioner, body wash, small toothbrush and small tube of tooth paste.  

Not sure how currency affects the investment though....something like 50% devaluation of the Yen over the last year or two. 

I'm looking for something repeatable (not sure how repeatable my commercial deal would be) that I can use for the next decade to build equity and cash flow.