If you've been able to hold a property for 20+ years, then you'll probably be okay no matter what the interest rate environment is at that point, since the property will be mostly paid down and the income will likely have grown a healthy amount.In my opinion, most everything comes down to your initial buying criteria.

When it comes to investing in real estate the primary benefits of the US market comparatively are 1. costs of debt 2. rent rates relative to property values (not in the Bay Area as much as in other parts of US) and 3. gov stability (which is perhaps a bit laughable right now I suppose).There are some incredible and easy ways to invest out of state, but it all comes down to having a "team" you can rely on (like @David Greene talks about in The Book on Long Distance Real Estate Investing.   

The only think negative I can say about Buildium is that their customer service department must be a pretty toxic environment: They are defensive and for the most part start with the premise that the customer must be doing something wrong.

I've used the direct mailer approach to find off market deals, but in this competitive environment everybody is doing that.

Incredible REI Strategy.

Any advice or direction would be incredibly valuable to me regarding possible entry strategies from people who have been there, done that.

Military benefits are incredible if used correctly.

Thanks @Andrew Postell that’s incredibly helpful and generous.

I'm interested in adding all of these to my portfolio at some point in time, but just looking for others thoughts as to which makes most sense to pursue given today's economic environment?

Could’ve been in a much better situation and would’ve purchased when the market was recovering and prices were incredible!