There's a concrete slab at the base of the stairs out the back door that goes into the driveway some and then oak tree roots themselves make it a little bumpy ride.

This in turn pushed the lender back from the deal.

We were trying to push the limits on comps, which we did, but not enough.  

Take this for what it's worth as I have a tendency to push the limits too far, but you're in the drivers seat here, ask for more.

I f he's treating you this way then he will treat other potential buyers the same way and you need to be the buyer that keeps pushing to get a deal, if it's a good deal. 

Good tenants are out there, but why replace one or push one if it isn't necessary?

A few may try to push back a little, but its not too much where they get offended.  

I don't like vacancy just because I want to push limits.

My belief is that portfolio/fund managers push diversification because they know the average investor cannot have the depth needed to invest wisely in multiple fields. 

If you don't have any expectations for career advancement then pushing the boundaries would be acceptable, however, if career advancement is your goal then sharing an outside interest which could detract from your job is usually not wise.