Are there any issues with his apartment that would lead you to believe that the maintenance expenses will be signficantly higher than the other units or is it simply dated/messy?

When we get maintenance requests or any other kind of tenant complaint, it goes through the Buildium system and gets attached to a particular tenant.  

This deal is not going to be accomplished safely as most approach an option to purchase, your agreement could well be 100 pages or more, addressing terms of sale, how liens for advances are applied toward the purchase, your interests acquired prior to other liens filed, insurance assignments, that's not counting lease assignments, attachments of lease terms and conditions, maintenance agreements and schedules, authorization to encumber the property and to pay liens.

We know the value of having a long term tenant, and also the value of having few repair and maintenance issues. 1) What is more important- a long term tenant or a recently rehabbed home.

There are also ongoing costs like accounting and maintenance costs for an LLC. 

How much deferred maintenance has gone on and how much are you going to have to put into this property to get better rents?

I'm going to focus mostly on the landlord side and financials, and my husband is going to be the handyman/maintenance guy and will be completely remodeling the basement on our half of the duplex.

You have to pay PITI and maintenance on a sub2. 

What about maintenance expenses for the septic system and well pump(s)?

What about maintenance expenses for the septic system and well pump(s)?