Sounds like they are under feeding the bull which is causing the bull to knock fences over and seek out food etc

Purchasing lower-level units without owning the units above can cause major issuesWhat Happened? 

Cause he isn't getting 1c for this while in Republican control.

Will this cause any red flags as a closing cost?

And the bigger benefit to this one is that simply purchasing land may cause you a depreciation recapture issue.You've got some really good options and with a little time and strategic thinking you won't have to invite Uncle Sam to your retirement party.

In my opinion the student loan crisis will be the root cause for the next recession. 

I like the strategy of doing evals 2 times per year that allow the tenant to pay for any damages they've caused so you're not having to ask for it at the end.

@Linda Chanthakhinh No harm in sending a contract to the seller to see if it gets a response. 

Anything more than that causes real problems with cash flow. 

The line in your original post "I'm a first time investor" would cause me to recommend you not taking on a project of this magnitude until you have some experience.This could work out great or it could be a huge money pit.