On an individual scale, when encountering an asymmetry you make the choice to absorb or outsource that risk.

This is a rather large deal to get into unless the experience is there..

The answer to your "fully occupied" question likely depends largely on the Owner-Occupier vs Investor market in that particular neighborhood (eg. desirability of school district).

Because otherwise, you'll run into the same problem anyway.And by "the majority of that back", it largely depends on how good a bargain you got in the first place; but sure, 70% of your outlay should be doable (once the first point is ok).

A lot of investors like Multi  unit properties for economies of scale, and diversified risk. 

Like all members of the BP community, I have goals and ambitions (Laughably large and ambitious to some/honestly most) for the life and legacy that I plan to leave.

Even at my rentals where tenants are responsible for lawn care I will clean up any large trees or branches that fall. 

If it is a master planned community with a large common areas (perhaps a pool) and extensive landscaping could also be in that category.   

I've also see very large variation in bids with the highest being more than double the lowest.

Most investors use LLCs for an entity but to really decide you should probably talk to both an attorney and CPA.You have not included a lot of information that would be relevant to the decision: - Do you have a net worth large enough that you are a target, so need an entity?