Listen to what she says and be hyper focused on those aspects first.

I’m just trying to understand as many aspects as I possibly can.

I said deck, I should have said front porch as that is all it is, with the start of the gable roof over it.

In order to do that I would need to put mini-splits in each unit, currently have window ac,  get new windows, new roofs (already ordered) update kitchen, bathrooms, furnish the units, and will have to do 1 by 1 because I need to wait until the tenants move out, etc.  

I know the weather is especially rough on roofs - are there other things I should likewise put a larger focus on?

For the latter, only thing is if the inspection show something unexpected (eg needing a new roof when it is obvious that the current roof is toast won't fly) or it appraises lower than your offer.

You can filter by the beds and baths and other aspects to make the results as close as possible to the one you're comparing.When I build my semi-automated hotsheet for investors, I take exports from the MLS from both the sales side and the rentals side, pull them into a SQL Server database, do some data cleaning to screen out as much of the garbage as possible, and run what I call my "magic query" that joins sale listing locations to rental listing locations by a conditional match on subdivision and beds/baths, or the average of the entire MLS if the subdivision is given as "METES & BOUNDS", with a flag in the output showing that those M 'n B rental numbers are MLS-wide averages for a given beds/baths and will need a more in-depth evaluation (like rentometer) if the estimated cash on cash return for a classic 20% down scenario, looks promising. 

This is the single biggest reason to own both sides of a double unit.The risk you take on is that you no longer share the expense of the normal "shared expenses" such as a new roof, driveway, etc.

If you want to make sure they're done, do them yourself.....I like the 'bonding' concept as well.... this visit will also give you a chance to check for small leaks under sinks, any damage caused by tenant, go up and check out the roof penetrations, check around the siding for a good seal at openings, Etc, Etc....Go online and find a home inspector checklist, that will give you a rough guideline of things to look for....

About 5-7 block up from a pretty bad area.We've been in this house for 10 years and have re-done all wiring, plumbing, insulation, roof, siding, kitchen, bathroom, etc.