However, since you have loans on two properties, you'll want to check with your lender about any due-on-sale clause that could be triggered by transferring the properties into an LLC.

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.

I use mine for storage of beach toys, drying rack for swim suits, storage of extra supplies and on occasion it’s an extra parking space.  

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).

I've recently been getting ceiling paints that go on pink and dry white to make it easier to see what spots were missed.

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. 

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

@John Bertolon we’ve noticed over the years that any decent rent increase triggers “stupid-trip” repair requests, change of owners or not.

Your sarcastic answer isn't as cut and dry as you think...