But I would love to start and eventually have some STRs out of state that generate a more passive income, vacation home, and maybe retire in it one day. 

I'm glad to be here to network and learn as much as I can, and eventually be a professional providing advice to new investors.  

Every landlord eventually runs into the issue of late rent payments.

Our current roadmap is to flip houses, pay off the HELOC and eventually mortgage.

Eventually, Class A property values increased to the point that even increasing rents didn't allow them to cashflow upon purchase.So, the flood of new investors switched to buying Class B properties.

They say the market always get's it right, eventually.

Currently I'm on the active side with the goal to eventually be fully passive.

Has anyone done something similar, buying property near a university for their kids to live in and eventually turning it into a rental?

Right now I’m growing my investment portfolio and preparing to launch service-based businesses (like cleaning and moving) as a stepping stone into real estate.My long-term vision is to scale into rental properties and eventually farmland, creating multiple streams of cashflow and a lasting legacy.

Have you found lenders flexible with draws, or do you front more of the cash?