I am setting myself up to buy a larger unit soon and want to do so in an LLC.

I think that the larger annual income is better.

A person who has invested anywhere from $10,000 in one 50-unit deal to twenty investments (or even more) of $100,000 each (or even more) in 250-unit (or even larger) apartment syndication offerings. 

You could scale into a larger deal, get a preferred return with a lower risk profile, and possibly get bonus depreciation the first year as well.

Take the gain now and keep rolling it into larger primary home.

This covers property tax, income tax and larger maintenance issues.

My business plan is to start with small multifamily (duplex, etc) and eventually build this into a larger portfolio of large apartment complexes (25+units).

Just pointing out that from my perspective he is asking how to structure what is essentially a partnership, and you were advising on paying a contractor to complete a task.

What is everyone preference regarding having the option to own a handful of properties out right verses having a much larger portfolio with the debt that comes with it?

What you need are comparable closed sales that are same or larger square footage with your higher price.