@Michael Johnson - I think like others pointed out above, you just have to be prepared for the extra work and figure out if the higher rent is worth the extra paperwork and inspections. 

What I didn’t know is that I would have to spend an extra week there just waiting for my flight out.

I could still account for this, but it just throws a lot of extra unknown into an ARV estimate.SO... should I pursue slightly more creative financing to make a winning offer and pursue this in earnest?

either with a cash out refi or to rent for extra cashflow? 

Then add in closing costs, etc. and you might walk away with a few extra bucks to plant new flowers at the 8-unit.

He wants to buy a new car and put it up for rent so he can make some extra money.

I know a 1031 is still possible under the installment sale, but honestly I don't see the seller going for this with its extra complications.

Then you’d want to budget for providing minimum service to condition that extra “interior” square footage.

The extra $5000 doesn't seem worth it.

There are shortages on everything right now and anything custom is likely to take extra time.