This is what I recommend for you to get started in your real estate journey:1.

I would recommend looking at how much money you could make as a STR vs LTR & then deciding if it's worth the effort to do STR vs LTR. 

Does anyone have recommendations on a platform that solves for this issue and is also user friendly for the tenants?

If you're planning on keeping properties as LTR, I HIGHLY recommend Heather Turner's (Brandon's wife) book on managing rental properties.

It's great to have you here.Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/m...Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/a...Read Beginner’s Guide: http://www.biggerpockets.com/r...Check out BP Money Podcast: https://www.biggerpockets.com/..Wishing you the best

Do you have any real estate agents, with experience with OOS investors, that you could recommend?

Even the American Institute of CPAs (AICPA) recommends that their CPAs get a cost segregation study done on properties over a purchase price of $750k.

Hey @Michael Martin, at 55 with a plan to retire at 65, most advisors should recommend debt pay down and more conservative investments as you enter the wealth preservation stage of life.

If you are thinking about doing hard money lending, I would recommend getting a competent attorney to draw up the paperwork.  

@Anthony BeltranStrongly recommend against this.