If I don’t plan to have any financing, As I see it, I will need to put in extra money to get from the $388k to the total required $533k.

It will have verbage covering them due to delays beyond their control , extras , etc . 

Its face to face that is more difficult.  I

We are entering the game with our first rental (family member was supposed to move in but passed away, so we already are in possession of this property). It's a very small 850 sq ft, no basement SFH on a street of nea...

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

We are using a property management company with a local office on HHI, but they take 25% of our monthly rent plus a few extra fees.

So 15 years down the road when your property is worth $100k more you aren't going to be worried about the $20k extra that you paid upon purchase.

I'd also like extra cash as reserves to purchase an investment property in the near future.Question: Since I already have a great rate on my loan now, would it make more sense to apply for a HELOC and access the money as needed?

In a competitive market, finding a good deal might require some extra time, and creativity.

How does it work if the neighbor reimburses me 100% out of pocket and then I submit a claim and get extra reimbursement on top of that?