From your perspective then as somebody who I presume understands it in and out, have you yourself used this strategy on an investment property.

If the loan is being paid off, the mortgage company would presumably not have an interest in whether the roof is replaced or not.

But as far as selling or not, there will be less impact on price before new regulations are announced, than after, presumably.

FNMA (and presumably others) guidelines actually address the scenario.

You now have $5k in unreimbursed expenses, and 2 houses; one with a $200k mortgage worth $250k (giving you $50k in equity), and; one with a paid off HELOC, value and mortgage unknown, but presumably with more than $165k in equity.You should also treat the $5k unreimbursed renovation cost as a debt and pay it back (even to yourself) accordingly.There is no tax due because not only did you not make any realized gain, but there was no sale. 

I have tried to send several letters to the address on file and even a post office box that is presumed to be related to the property and all have been returned to sender.

Jesse Brown Since you live in the most expensive area in the country, can I presume that you intend to execute this rehab & hold strategy from long-distance?

Given your presumed lack of real estate experience, OPM (other than 'traditional' bank financing) is likely off the table for now. 

With rentals - it's cash flow every month for as long as you own it (presuming you find a good rental that cash flows - which isn't the easiest thing in today's market.)Know that you are coming into a high market - both real estate and money are expensive right now.  

And I presume that you can find good podcasts, YouTube channels, etc. - for as narrow or as wide of a net you may want to throw out for your own “real estate investing.”But if you should still have an inclination to trust some guru with a paid mentorship, I’d suggest to go above and beyond their standard contract, which will likely stipulate what you owe them in far better terms for themselves than what they owe you in return for your money: I’d ask them to stipulate - in writing - what “mentorship” your money (at each level of a “workshop”/“education” they expect you to pay for) will actually get you, and for how long.