Same when I look at the public records, it will come as a Single Family Residential in the Land Use description (it does show Duplex-Triplex in the Built Use/Style description).So how can I refresh my search that can include both units (#1 and #2) in the address so it doesn't exclude the ones describe as SFR?

You could definitely run 1 outdoor unit, but you will need a few indoor units, depending on the apartment's configuration.

My contractor is recommending the house be resided with some T-111 because the bottom part of the siding, about knee height and down has some rot and he doesn't think we can find the same style siding to match.

I like this style for the following reasons:1) I require a parental guarantee - no payment issues2) I sign one year leases - I start inquiring to my students in February to see if they will renew (100% renewal for those not graduating so far) which keeps my vacancy rate at 0.3) I require a group of students to rent the house. 

The owners put "hip" style trusses on the top in hopes of giving it more height and a better curb appeal. 

Except of course if there's already too many hair salons, or everyone starts preferring long messy hair styles, or your state legislatures impose a $10 per haircut tax, or we realize that electronic clippers actually cause cancer.Relative to doing nothing with you money, real estate is likely going to always be a "good investment". 

There is no precedent for appreciation with that style of property in this market.

Can you make a universal style contract that can just be filled in for every deal?

The home had a jack and hill style bathroom with two bathrooms connecting to each other.

The big ones are replacing windows (historic district people go absolutely insane for old-style single pane windows), replacing roofs and siding, and doing any kind of addition.