Offering a lower bid will just cause it to be rejected and even if you got the deal, the few dollars would not be worth ruining the relationship with a realtor that actually brought a good deal on your table.2.

I am hoping the property management company will handle the hassles for me, and keep a steady tenant that won't ultimately destroy the home, ruining its value. 

If it doesn't we won't be ruined, just very low profits until we get both units renovated and the rents up.

In Newport News, in particular, there are tons of condos and town homes that are attractive but HOA fees can ruin an otherwise appealing buy and hold deal. 

The potential insurance rate hike can ruin the  numbers from one year to the next and once you pay huge insurance amounts, you can sell the house only with a steep discount.

Having a bad tenant can ruin a whole building of tenants.

Is it permanently ruined?

The other scenario for landlords I'm sure has been devastating, losing money, trying to get federal help and those not paying rent more likely to ruin the home. 

At least that way (like others mentioned) you can, if you choose to show the sell that the numbers don’t work out if you were to offer more and you weren’t try to insult them.But as a side note, and I don’t mean this as a direct insult to anyone here that is a broker (because I don’t know any of you personally) but I have dealt with many, many brokers over the last 30 or so years and even had a major issue like what I am about to say, with our own personal property purchase, but sometimes brokers can either ruin a deal or even worse, can lie through their teeth and attempt to sabotage a deal if they feel you are not offering enough because that means their commission will drop too.

IMO, I rather pay someone that I can easily fire if they are doing poor work, then ruin a family relationship.3) If you are planning to do any renovations keep in mind that winters are long.