I'm hoping I didnt make a mistake with these numbers but assuming proper assessment of the local market, jobs/population growth, property condition, rental demand, future appreciation etc., is this something that sounds within acceptable ranges or am I missing a piece of the puzzle here? 

The one I got was okay at first, but as time went on we had more and more special assessments for repairs. 

The HOA fines will be assessed against the unit and therefore the owner.

Properties in highly desirable neighborhoods during a seller's market can often result in buyers taking a property as-is with little/no room for negotiation.The fact that they're agreeing to: a lengthier inspection period; paying for a structural engineer's assessment (Roughly a $1,200 value in my market); account for a repair budget; etc are all good signs.If you're getting this below the average value of comparable sales, it cashflows, AND you'll have peace of mind with necessary repairs & inspections, I'd say go for it!

I am hoping this foundation expert is wrong in his assessment.

Furthermore, understanding the resident characteristics allows me to measure the target market and modify my investment strategy accordingly.Inspection ChecklistSituations vary from one property to the next, but here is an on-site inspection checklist to get you started:Interior Units:Inspect vacant units, including one of each finish out type (Classic, Reno, etc.).Check all down units.Inspect one unit from each unit mix.Exteriors:Landscape:Look for overgrown bushes.Identify trees that need trimming (no branches hanging over the roof).Take pictures of the following:Curb appeal on all sides facing the street.Landscape around the office and amenities.Overgrown bushes or trees.Any dead landscape.Areas that may need sod or mulch.Assess drainage:Ensure water flows away from building foundations.Check slope, gutters, downspouts, surface drains, French drains, etc.Exterior Walls:Determine the existing material (wood, vinyl, Hardie, brick, stone).Assess the condition of the walls.Note if painting is required.Take pictures of each building, including building number, each elevation (clockwise), and any breezeways or niches.Windows:Evaluate the condition of existing windows.Consider whether solar screens should be installed.Roof:Identify the type of roof.Assess its condition and age.Parking Lot:Check for potholes.Assess the need for restriping.Note whether the parking lot is concrete or asphalt.Evaluate drainage issues.Walkway:Look for tripping hazards.Assess drainage issues.Foundation/Gutters:Inspect for cracks in the brick.Check for separation in corners from fascia and trim boards.Evaluate drainage and identify poor drainage areas.Amenities:Identify possible improvements.Consider adjustments or additions that can enhance amenities.Talk to the Staff:Maintenance: Inquire about the physical condition.Office: Discuss current residents, delinquency, and potential changes to add value.Assess whether rents are too high or too low.Confirm rents and what is included/not included.Confirm other sources of income and associated charges.Confirm occupancy, pre-release, and vacancy numbers.Note: Maintain professionalism and avoid insulting the owner or broker, regardless of the property's condition.Keep in mind that investing in real estate is like solving a puzzle—you need all the pieces to see the big picture.

Very helpful question that I'm curious to follow - my suggestion would be to work with a local tax professional + 1031 qualified intermediary to better assess your personal situation. 

If you look hard and in the right places it is not inconceivable to get a much larger discount.Ability to assess value - I honestly don't know much about stocks and companies and market valuations...

@Michelle Curran - Here is a CSS Decision Diagram flowchart intended to bring together all the various questions when assessing the benefits of a CSS (via a professional or DIY).

So back to general knowledge, what I would really be assessing is first: what do you actually need?