So my thought was how to invest in something where I can store my toys and make out in the end.

I hope to one day get a vacation house there but it would be a "toy" and not necessary an investment.

Men like their toys.

Due to the negative cash flow he is having to come up with an estimated $182.50 a month over the long haul.  

I have actually been toying with the idea of doing the same thing.What you are actually talking about is starting a business and not necessarily just real estate.

I started with Quicken Rental Property manager and soon realized this is a toy of limited value for me.

I tell my RE agent to tell the seller that I will pay to have any remaining items removed from the house and pay for a U-Haul if they close on the 9th.February 2 - RE agent calls me and tells me that they want to keep the February 29th close date because it would be too hard to "alter their schedule".  

I would love to tell you to be warm hearted and give them a desperately needed break but,your rental doesn't sound optimal for her poor health to deal with safely.They need a one level ground floor unit to keep her safe and you away from a potential lawsuit.The first time she tumbles down the stairs and gets hauled away in an ambulance you are going to hear from their attorney crying "Well you should never have rented to them you greedy slumlord!!"

However, you can never renegotiate the price of a property after you close ... you're into that for the long haul.

I am looking at taking it to the next level and have been toying around with the idea of some 4 unit apartments.