The  unit is rented consistently and is functional but also needs upgrades, new siding (has 2 layers), Some rooms could benefit from re-wiring and more insulation,   Painting is always an issue as it is not plaster but older thin wallboard. kitchen is fairly new, bathroom could use upgrade, upstairs bedrooms have some pitched ceilings but I don't think based on the foundation/construction it is a candidate for a full second story and it had a new roof a few years ago.

Ins is through the roof as well. 

The value he adds to you can increase substantially and save you a ton of headache.An experienced investment broker will aid you in all aspects that come with the deal like underwriting, valuation, potential, structuring the deal, etc. 

The appealing aspect here is the ongoing population growth and other economic factors.

Our roofing guy has done 3 roofs for us and got many other jobs just by word of mouth recommendation.

I get the comfort aspect, but are they bringing the value that offsets their cost, given the availability of tools to enable remote property management? 

You can get rid of many of your annoying little 'old-house issues' by buying an existing house that needs repairs and literally doing everything: new plumbing, new electrical, new drywall, new roof, etc....

There will be a lot of no's but there are still ways to get them talking (it's in scripts - "Not even for $$$", I'm not calling to lowball you or waste your time", "I'm really just planning for my next one in the next 3-6 months"Get to the details like Capex - age of roof, furnaces, water heaters, central ac units, electrical, any recent updating in kitchens or baths.

It doesn't take too much to live with a great deal of creature comfort when you don't have to pay for a roof over your head!  

My wife’s stress level has been through the roof.