His good customer service convinced us to go with Kiavi over two other vendors offering similar rates.

Anyone that has sold items privately would have countered any offer. 

Instead of stressing over timing it perfectly, focus on making sure the deal still works even if rates shift.Since you’re buying in Norfolk, check if lenders there offer any investor-friendly incentives.

You've signed up for one PIA if the owner is still in the house.One way to tippie toe into this is to hook up with short sale agents and start working with them offering to door knock the NOD folks. 

I initially offered $200K in cash, but the seller countered at $240K.

they usually say stick it in the bank.. so you can offer them a nice return above bank CDs and on an asset they already know and like etc..

Did the insurance get cancelled in this case. 

Rhino is an insurance program, and I do not recommend them.

Make sure to account for property taxes, insurance, and any HOA fees, as those can vary significantly in different markets and impact your cash flow.

They are asking $375K but not getting it - so not quite $20k underwater from asking but they're offers so far are around $350k and lower.