I understand I can qualify for an FHA loan, but having a larger downpayment is ideal for me.Any input is appreciate.

The sellers I deal with don't want them on LoopNet and CREXI though.

My question is: as an aging tenant and although she is healthy now, if she were to develop a disability due to aging am I supposed to make accommodations for her such as adding wheelchair ramps or converting bathroom showers and tubs to better suit a disabled person?

These goals dictate the ideal asset type, in may case, single family homes.If you understand duplexes and they support your goals there is no reason why you should venture out into 4 families, which are typically lower rent per door. 8 and 12 unit buildings are different animal all together and in a way the worst of both worlds - these "mom and pop style MF" have lot of the disadvantages that come with MF, but don't give you all the advanatges and synergies that you get with a "real" MF, say 75 units and up with professional on site management etc.

Ideally, I would like to purchase a place ahead of time and transition into for retirement.

Am I understanding correctly that your ideal plan A scenario is to hold the property, and then the fallback plan B option would be to possibly resell the units 1 by 1? 

Networking is also not my strong suit, but I am good at analyzing information, so there is a good chance I am over analyzing things and I just need to get out there to my "uncomfortable zone". 

As soon as you start hearing a client use bigger pockets type terms, like "house hacking" or "brrrr" or "1% rule," you want them with a LO on biggerpockets.com, no one else knows or uses this peculiar vocabulary, ideally you want everyone speaking the same language.

I suspect more phone calls to clarify their records on each property I deal with.

My ideal scenario would be to attack fixer uppers in one market and turn it over to a management team.