Also, I am thinking of investing into real estate via a new Self Directed Roth Solo 401K account due to tax free distributions after age 59 1/2 instead of SEP IRA, any thoughts? 

Your referencing effective age vs chronological age. 

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.  

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

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.

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 recieved my real estate license at 19 years old, and you will face difficulty in closing deals due to your age as I did.

@Andreas Mathews,Good for you at looking to make a change no matter the age.

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.

My son (age 24) however, is an independant contractor / self employed and is trying to buy a house.