It's probably best to have them pay out of pocket for a smaller cost like this.

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

This would likely take coordination with a tenant at some point - (ie - plenty of notice to them that they must vacate in order for you to sell the property)Since your current home is free and clear -  you could do a cash out refi or take out a new mortgage on the new house to be able to buy your paren't house and pay off the mortgage.  

Even with renovation costs and insurance costs the fix n flips are still making money.  

They cost slightly more than the normal permitting process, but I usually have permits in hand in a week or less.My GC is has some experience on Coronado, if you would like I can connect you, so you can get his opinion as well.

Always have a clear exit strategy, whether you plan to rent, flip, or sell the property down the line.If you or your son are looking for more hands-on guidance, feel free to reach out directly.

Please feel free reach out. 

The cons, if the borrower doesn't pay on time or completely welshes on it then there's that oportunity cost. 

I bought 14 houses basically for free by harvesting the equity in my houses by doing 5 cash out refis.

Again I cannot collect rent to justify this cost/effort.