If you prefer to close on as many as possible but don't necessarily need all, then one contract for each with no language linking the contracts would be smarter because you can bail on any that have serious problems you don't want to deal with.There is a lot of experience and knowledge on this site, I expect you'll get other food for thought as well.

So I'm looking for something between $40 - $50k that is pretty much rent ready (preferably tenanted).

If you mean gurus or even a guru with a law degree, I can assure you, they are not finance experts.       

Some snippets:...our office remains skeptical that all of the shift into rental is permanent, even from a taste or preference stand point.

I would prefer to stick with someone local if possible, but you certainly make good points.

I'm hoping to buy a multi family (preferable a tri or quad plex) in the coming months and I'm heavily leaning towards getting a FHA loan.

Am I putting to much personal preferences in this?  

As a borrower, I can assure you that you don't want all your eggs in one basket anyway.  

So there are many more choices of properties to purchase in the SFH category.I have both SFH and MF, but also prefer singles.

Personally, I prefer to handle the entire tenant placement process myself for the following reasons:-nobody will care more than me-I have processes in place for all aspects of tenant placement (so I don't need to spend any time learning how to do it)-I like to meet all the prospective tenants in person (meeting in person vs. on paper or over the phone can be very important and effect your decision)Again, that is just my preference.