For example if she is looking to retire and the property hasn't been her primary,  a pro for her might be that owner financing decreases immediate tax impact for her.

Also, slightly changing what you have proposed might also decrease your tax fling obligations especially when you are in NY.

My recommendation is to find something where you can rent 1/3 or 1/2 of it right away so that you can supplement your income or decrease your negative cash flow to make your savings last the longest. 

I personally make my properties kids friendly to attract families, this decreases my chances of party people and other bad guests.

If you're renting, try getting a house/room mate and subleasing to them to decrease your housing expense. 

I'm definitely not against it, only thing is I have to stay in this area as I work in a trade and if I move to a cheaper area unfortunately my pay will drastically decrease. 

It seems like there is anywhere between .5-1% of an decrease in 'fees'(?)

Maybe you could decrease the equity you pull out, which would lower your payment so that you can still cash flow?

Do you recommend getting good insurance to decrease the risk of home wreckage?

Do you see potential for rents to increase in this area given the growth at EB or can you see rents staying steady/decreasing in the 5-10 year time frame?