Be careful not to place your identity in your age/success in RE.

Congrats on your maturity at a such a young age.   

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

In my eyes, everyone is truly soon-to-be accredited, my goal after meeting Dave at age 22 was to be accredited by the age of 30 (income and net worth) and if I stay on track I will be!

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.  

Given their age and position in life… mailbox money flow forever sounds like a good start to retirement to me!

However, short term rentals are much less passive than long term rentals and are essentially a hospitality business, which is in and of itself required a whole additional layer of knowledge and expertise.With regard to your question about private lenders, it’s important to draw a distinction in terminology between “private” and “hard money.”

I fund land flippers in all these states and at your age I would be hunting down a parcel now U want to eventually move to...

For us approaching retirement age, we want to have a mix of mortgaged properties and properties with full equity to leverage instead of relying on saving up for the next investment. 

@Raul VelazquezI would suffix what others wrote by saying that you need to understand that real estate really is a longer term wealth strategy - even though that is what you say you don't want due to your age / starting point.