I have the funds to pay for the roof replacement, and I would pay for it ahead of the actual purchase, but hate loosing on the tax depreciation on installing a new roof since I'll be paying for something I don't own.

Is that not a flagrant violation of the duty of loyalty that agents are bound to? 

I understand at this point there will be a loss I will have to incur, but I am looking for thoughts on if I should rent (knowing I’ll have around $5k a year to loose with renting and property taxes , but giving myself time/ hope of appreciation) or if I should just sell (locking in a larger loss on the property now).

9) adding multiple ADUs or adding an ADU to a quad looses F/F conventional financing.

Prices wont come down enough to justify buying as a rental, rents could be rolling over and interest rates will be range bound for a long time. 

You CAN NOT target motivated sellers.The only way to get in touch with motivated sellers is for you to make it extremely easy for them to find you.Going after lists will be your doom.If you have $30K to spend on lists, sure, due to sheer volume you are bound to get a deal with some luck, sure.But if you come along with a humble budget, forget it.The reason larger budgets work better is because you can send a huge volumes.

It is unfortunately not made out of reinforced poured concrete and instead stone and mortar that could become loose from too much ground movement.

You're legally bound only by the agreement you've signed with your agent. 

Almost negative on cash flow with all these repairs coming all the time.Next major thing I see is hvac in crawlspace and those ducts are loose and coming off.

The lawyer looses all reputation.