plan on moving every 1-3 years and getting a new property to house hack. 

I own a home which I’m currently living in and planning on making a long-term rental property as well once I move out.

I also like to find win-win scenarios for seniors looking or needing to move into some level of assisted living.

Don't want to pay tax on selling the rentals I unfortunately don't think they actually want to utilize the 121 to sell their existing primary and then potentially buy another one-it sounds like the goal is to ultimately continue owing that initial home which I think makes this whole plan 5x more likely to be torn apart under audit because they're trying to end up with the same property they started with.  

If you and your fiance are willing to make a couple moves and remodels you could put yourself in a very strong cash position. 

This allows you to invest in the locations that offer the best ROI and make the most sense based on your goals where you can be a bit more passive in your investment property.

What was your goal and timeline when getting these properties?

Yesterday I found out that my old neighbor who moved away to take care of her father, inherited the house next door upon his death. 

However, your goal should be to make instructions/communications/labels/etc. clear enough so you get few calls and just a handfull of messages. 

With a decent amount of equity to start, I’m exploring the best, way or ways to move forward.