If you want to market the certificate, then you market it as a tax certificate and see if anyone wants to buy it.If you got a deed then you need to know if it's insurable or not.

Not to mention upkeep (repairs, taxes, water, insurance) of her personal property (reverse mortgage) and mine.

The owner is 90 and has a few family businesses that are stables in the community and puts all his attention into those and does not really have the interest in dealing with everything that comes with tenants, renovation, and what it would take to bring the property up to market value.

If you do things by the book, provide habitable housing and insure yourself you should be fine.

I also know great people for home insurance policies, a great loan officer etc.  

Currently renting out the old primary residence at $1800/month with a cashflow (after mortgage, insurance, taxes, vacancy, maintenance, cap ex, etc.) of over $500/month; with the other two investments each pulling in between $250-350 a month.I also decided to make tennis my "full-time" job and pursue real estate more heavily as my career.

Expenses: holding costs such as utilities, taxes, insurance, lawn, snowCity fees - permits, potential fines and assessmentsLending fees if anyI would get an attorney involved and write up a partnership agreement that you're both ok with.

This was really the worst possible sort of storm as far as insured losses.  

This rent covered all expenses on the 15 year mortgage, insurance, and HOA fees with small profit that got eaten up on paper by LLC expenses, depreciation, PM and accounting fees, etc.  

I have sold insurance to many of Federico clients and he always seams to find them great deals.