He got married and we were very strategic that we keep each rental property owned individually so they can each have 10 which would be 20 combined. 

Modern solar technology is a far cry from what it was in the 80's in terms of efficiency, price, everything else.  

She is 73, has no money, I made her retire (not educated in modern world, skills aren't useful, works more detrimental than what its worth), and I essentially turned this house over to her to live her life in.

They will also be able to combine several types of lists so you have a good mix to mail or call.

Combine that with a hefty LIRR fee, and lack of commuter parking, and you get congetion issues which force owners to sell in Li and buy elsewhere, further away in the island, somewhere by riverhead or outright not in the island.Rents are high, which is a good thing, but I am not sure if it would be wise to throw a huge portion of the rental income on property tax, when it could go into your home.

@Trent Lee I look for cities that have the best combination of cash flow and good economic/demographic trends.

Starting a new job in the next two weeks that will start me at roughly $40k (current job *2 jobs* combined makes about 34,500 py).

Sure, anytime you can provide combined services for logical complementary products there is demand.

@Ken Martin  The seller is going to get their equity through a combination of your down payment and the principal + interest monthly payments. 

However, a 10 lb dog visit for a day (and not staying over night) combined with reasonable, responsible tenants who respect my rules is a situation where I feel I could make a reasonable exception to the lease and keep happy tenants who will likely stay longer and continue to disclose any actions that would need my permission rather than doing as they please behind my back.