Your referencing effective age vs chronological age. 

They are starting to age out.5.  

@Larry Bailey59 years young is still a great age to jump into anything!

Ranking in order though...1) Prices will drop - 10-20% because the job market is getting tougher2) Salaries will increase - 3-4% per year to keep up with inflation3) Interest rates will drop - 100-150bps as people worry less about inflation4) Unfortunately, the dream of a house with a white picket fence will be out of reach for many, especially before the age of 40.

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.  

However if you have enough reserves, 6mo or greater then I'd say chance it but a couple of missed payments from the tenants and you have to foot the payments out of your own pocket.I'm all for taking risks but I think you really need to evaluate the age of the major systems so you don't get hit with a bunch of cap ex all at once as well as your reserves. 

I would say the condition and age of the property would have a lot of sway in your decision for whether or not it's worth it.

In Reno and metro areas, insurance companies primarily focus on roofs, the age of the building, wiring updates, and water pipes, as mentioned @Cameron Moore.

Short-term rentals are becoming oversaturated in certain markets plus anti-STR legislation is resulting in some of those properties also converting to long-term rentals.You already have the operations experience by self-managing.

I wish I got started when I was your age.