So the benefit to the investor (aside from being a good person and helping out the elderly!)

From that point you make the decision based off their value (essentially the benefits they offer - the cost.)This is not legal advice, just my opinion as a real estate investor.

You can only benefit from this exemption once every two years. 

Three are some programs which area specific which can benefit to first time home buyer but those program goes up to 2 units max.

I currently work in financial derivative compliance and regulation, so hopefully my specialized knowledge will be of benefit to the community at large.

Do you want to plunk down down payments in return for monthly cash flow, tax benefits, and principal pay down?

Neither of us have broached the topic of renewing their lease term, so at this point I'm assuming they are planning to stay and would like some extra time, so I thought it might benefit us both to end the fixed lease on 6/30, and then start a new month-to-month lease with a 1 month term and 30 days notice, all on 7/1, with some language built in for their leniency on showing the place to prospective tenants.  

Is it not normal to negotiate terms upfront and change the agreement for mutual benefit?

Until you learn to separate what is related to your management company and what isn't you are never going to be able to properly analyze the benefit & expense of the product they are providing too you.

I'm not quitting my day job (the earliest would be 8.5 years from now to claim my pension and retirement benefits) but we will look for our 3rd source of income and take the long approach to transitioning out of corporate world.Too me, this is a Marathon, not a SprintGood Luck!