Depending on your personal assets (i.e. what your willing to risk), in the event a claim is made against your investment property, and how much RE you plan to buy long term, those factors should dictate whether you should get an LLC. 

(OR, once I've reached $1-2M in net worth I can cash out and live off an annuity.)Not sure if I'm thinking about that right, but that seems like the two primary "paths" -- not that they aren't interrelated, but it's relevant because it dictates how much of an appreciation play / vs / cash flow play you're going for.I'm 30, I'd love to make "the plan" to hit "the goal" at 50, that seems achievable, but I'm having a hard time wrapping my head around those 2 paths/end goals and how to "SWOT" the routes for achievability.

There's always added pressure on businesses to want to pay less but the market will dictate who is going to work those jobs.

trusses are a roofing component.If this is a condo, then the by-laws dictate anything related to structural issues...likely the association will need to decide what happens.Adding a bit of information on the ownership structure would be helpful. 

the terms of the leases in place will dictate what you can and can't do.Chances are there is only 1 water meter, and splitting it 3 ways is usually the beginning of tenant-tenant conflicts.You could probably give somebody a rent credit to take care of the lawn, but if the lawn is generally used as a common area for all tenants, the landlord usually covers that cost.You could always change lease terms when the leases expire - but as a rule, the leases stay with the tenants who are in the property even when a property is sold.

Depending on how busy the office will dictate one on one time with customer service.

Depending on  your personal family situation will dictate where ya wanna buy. 

And what the local rents dictate

Don't let the tenant dictate the terms.

Find out what is the norm in your state and do what the fashion in your area dictates.