Often times inspectors overlooked them as they are very small and minor but as you can probably already tell, they are extremely important and prevent water intrusion.Your best bet would be to contact a very reputable Siding/roofing contractor and have them go through the entire property and put in the proper drippage flashings seals and caulking necessary and have them insure the work. 

I've kicked around installing AC but still manage to get renters applying to live there before I pull the trigger on installing AC. 3 - 2nd Duplex - I installed central air after purchasing the property for inherited tenants but they've used their own W&D units for years.

One more tip – people remember stories that trigger their emotions.

There is an unfinished basement which will likely be permitted to convert into an ADU but might trigger the installation of a fire sprinkler system ($30k).

An extreme example of this is a property I once sold.

Self-managing from a different state is extremely difficult, especially in states where the law favors the tenants.

As a property owner, my experience with MNPMC (sometime called MN PropertyNerds) as a property manager has been extremely disappointing.

As mentioned above it depends on the metro but I would make sure I was comfortable with the LTR rate before pulling the trigger on an STR. 

A bit of a more advanced exit strategy, but one that can be extremely profitable when implemented correctly.We spent $18k to clean out the place and then we turned around and made $40k after cleaning costs, closing costs, and commissions.

The risks, such as triggering a "due on sale" clause and complicating your taxes, often outweigh the benefits.