Even if an employee of a bank has money to loan, you still need a phone number to talk to, make arrangement to meet in public. 

I would suggest you check the landlord tenant laws for your state to find out what your regulations are.In my state we are required to provide temporary arrangements for tenant. 

Oh Brian, you're going to keep me busy I see.Option greater than 12 months (or that has an option to extend beyond 12 months) is a financing arrangement unless you show the buyer has no intention to buy with good reason.

It is reasonable to ask tenants to make arrangements for rare, valuable, or fragile items, as most installation companies will have disclaimers against this kind of stuff, but I have had flooring installed in occupied houses before and the flooring installers - wood, carpet, and laminate - did all of the furniture disassembly, relocation, and reassembly.

With that said I know of a GC, but he's a partner on my deals so he'd most likely be looking for the same arrangement.

Plus, I have my husband on board to make sacrifice in our personal living arrangements in order to get closer to financial freedom (huge score!) 

Question #2, If I do allow my tenant to take in a new roommate, I am thinking it best to have him set up a sublease situation with my permission so that I do not have to deal with the new renter, the current renter would be responsible for arranging all communication with them, however I would provide a lease and ensure that I am 100% comfortable with the conditions that he is setting with the new renter.

In other words, will I sell the contract to the buyer with the due diligence already done, or will the onus be on the cash buyer to arrange for this?

It really depends on the arrangement you have setup.

If I sell it and would like to do a 1031 exchange, is it within 1031 rules to live at the new property if I will also be renting a portion of the property out, similar to my current arrangement?