If the stars align, this might allow you to get the best of several worlds - a larger, nicer asset that is more meaningful to your overall financial position, a great owner-occupied loan with a low down payment, and a potential for significant cash flow. 

So in a stars align perfectly kinda way, the best way would be a combination of the two you already mentioned.

Those details of course could be worked out later, I'm just saying that would be a component he needs to acknowledge there is some flexibility likely needed to reach a deal. 

It could be that they are doing all they can but the contractors are backed up… yes, their vendor list should be able to accommodate delays by switching providers but sometimes waiting for that one that knows your properties inside and out is ok especially if it is not an emergency - get your and their communication expectations aligned.

We replaced a toilet and have repaired/replaced components of both heating units.

So waiting for the market gods to align with better rates, more inventory, less competition and falling prices is never a good strategy.

There is also a distinct separation to keep in mind here, we are talking about the structure, the home itself, components are a separate item.

With two and six year old children in the home, I am concerned about unsecured posts and railing components on the deck.

Flights are fairly cheap (compared to property) so I’ve always flown out for my initial weekend search — not just to look at homes, but mostly to make sure I’m happy with the designated neighborhoods where I want to buy, and to make sure I’m aligned with my agent on my “buy box” criteria (using homes we see together to point out elements I want in the final purchase).

If you did, does the job expertise align with your area of study at college?