Is there any room to bump them up.Also I would still add 1-2% just to cover some labor even though it will be from one of your other businesses, in effect treating it like blue money.I would also try to offer less.

It is older (1985) and consistently rents with negative cashflow (~$150) per month.  

Does that effect its financial statements?  

Write them down and think of every aspect effected.

I can have someone periodically clean them up.. would that be more cost-effective than spending it on gutters?

Thirteen years later the real estate is barely back to what it was worth back then and it was massively negative on cash flow (mostly the land). 

But based on activity levels required by case law to have a T/B and some IRS pronouncements on the issue of NNN in related but not identical contexts (for purposes of determining if an international taxpayer has sufficient connections to the US to have what is known as "effectively connected income"), I'd say odds are high that NNN leases will not be viewed as a TB for purposes of the 199A deduction.

That would affect their psyche in a negative way.

I’ve spent so much time over the last 8 months learning how to effectively analyze deals, finance deals and manage rentals, but I obviously missed some things.

Overall, the idea is that you might be buying a building at a 6% cap rate (or less) but when you underwrite conservatively using market data that you know and are comfortable with, you can run the building better than the current owner, make the building cash flow and effectively making it maybe a 9 or 10 cap building.A good example.