I was trying to work with him barter/reduced rent to maintain property.

If you are capitalized enough to purchase, I suggest you hold the cash to maintain a strong credit profile and look for purchase + renovation funding.  

We are offering short-term leases through spring, maintaining the rents as is.

Are there certain limits I should be looking to maintain or lower to get a better price. 

Just because your personal lifestyle doesn't warrant being an occupant homeowner, doesn't mean you can't benefit from others with lifestyle needs necessitating a backyard but without homeownership, that need a housing provider (ie, you) to provide and maintain for it.

You are responsible for maintaining proper heat and cooling, but 70-72 degrees would be considered reasonable by any court.The problem with allowing this is that before you know it, every tenant has AC units in their window.

You as a landlord put yourself in a position of needing the relationship to be maintained.

My primary has no trees near and my gutters are always nice and clean and I like not having to maintain the gutters, plus I like being able to see a house in it's entirety, what does everyone think?

If this is an older building that will continue to need ongoing maintainence, than a 10 cap would be more appropriate. 

I would like to continue to grow our portfolio to a point where we can both go part time and off of weekend package, which would allow us to have an incredible amount of flexibility with our W-2 jobs while maintaining some great perks and benefits.