LTVs, minimum ROI, etc), therefore I knew that if the deal was comped out within our guidelines it would be a workable deal.

That is a much more workable model for SFH.

Please comment if the above is a scenario seems workable, especially minimizing the discount on the lower LTV first.

This might or might not be workable in your specific situation, but in terms of time, it is likely highly inefficient, but you also can learn a great deal about the neighborhood you are searching in. 

If your tenant doesn't have any flexibility, then the concessions you get from the seller will probably need to go to some temporary housing for your tenant for a month or you'll need to break your contract with them.It sounds like two families need housing for a month - this doesn't have to be the end of the contract, but I think that somehow the 4 folks involved - the two families, you and the seller, should be able to hash out something workable.

In terms of area, more specifically the location we went for is in the St Francis heights area a bit farther south which I think is a bit nicer than the northern part of Daly City (e.g. the Crocker area).My rationale for this area was (1) it is close to SF but does not suffer from all the rent controls and tenant friendly rules in SF itself, and (2) since it is close to BART, might be workable for someone working in city or in Bay Area but more value for money.My in-laws actually live in Richmond which is very nice.

Understanding the true nature of her complaint may lead you down a path to find a workable solution. 

But college rentals can be, too.Finding workable college rentals is difficult where I live.

But this is a workable strategy, if you can buy cheap enough.

If it were me, I'd put this one on the back burner and invest your time and energy into deals that are workable and make sense.It IS possible to work this deal, however your expenses to date are merely the cost of doing business.