Very part-time and flexible hours.

My option is that I would do this from the beginning for several reasons:1) Liability protection (consult with your attorney on this).2) Separation of business and personal credit (keeping your rental mortgages off of your personal credit allows you to be more bankable for any lending you might need such as personal mortgages, car loans, etc).3) Leveraging business revenue to secure additional business lending (such as business lines of credit). 4) Loan flexibility (there are several hard money lenders that have pretty good long term renal programs with flexible terms unlike most residential mortgages that will be stricter on some of terms such as where the down payment and closing costs $$ comes from).

It seems like these local credit unions are just much more flexible on how they do these deals. 

You have to be flexible in your market.  

Seems to me this option of splitting the condo and essentially renting two one-bedroom apartments could make more money, and  be more flexible, than only renting it as a two-bedroom, however, I don't want to go through the expense of adding the interior door, mini-fridge, microwave, etc if you think it may not pay off.

I'm currently looking for renters, but I'm so flexible that I may use it as a second home when I want to come visit Chicago or with the housing market being the way that it is, I may just sell it.I had so much fun with one and I'm looking forward to my next!   

If you have 5 bedrooms (and assuming you've moved out already), you might have 5 leases for each of the 5 tenants, as opposed to if you had a 2-unit property where you could just manage 2 leases (however, you could also rent each of the bedrooms in the 2 units if you wanted, but you at least have that flexibility with multi-families).Multi Family Pros & ConsProsLive in one unit and rent out the other unit (assuming you don't want to rent out the bedrooms in your unit as well)Easier to manage the leases if you are renting out by unitConsMight be a bit trickier for extreme cashflow because you're charging rents by the unit instead of by room (unless you choose to rent by room)You're not living directly with the tenants so there is slightly less supervision (but then again, you're eventually going to move out of the investment property whether it's a single family or multifamily so this 'con' is inevitable)All in all, the house hacking process is generally the same, but as I noted, there are some slight variations which lead to slightly different strategies.

This entails doing the legwork upfront to establish relationships with Banker / Private Money Lenders that provide you this flexibility. 

You can assert your stance as a professional AND be flexible to their advice regarding the project.

With a line of credit1. you are more flexible, and dont pay interest if you arent using the money2. usually pay less fees up front3. usually get processed faster4. can usually get interest only paymentsCons  1. they usually have floating interest rates2. technically the bank can take the money back if something happens and the money is in your account, such as a market collapse3. they usually are on 3-5 year terms, so you need a plan to pay them back by then For a Refi1. we have record low interest rates right now, you can borrow money and lock that in for the next 15-30 years. 2. repayment terms are spread over 15-30 years3. fixed interest ratescons1. higher closing costs up front2. you are always paying interest on the moneya lot depends on outside factors.