If you go back to fundamental and think about why properties/anything  goes down or goes up depends on Supply and Demand.

I looked and vacancy rate and comps using Zillow and and web search I didn’t see any concern.

You'll see lots of people saying stuff like "travel has fundamentally changed forever" and yada yada, but that's exactly what people were saying about work from home stocks and tech growth stocks last year and now a lot of those are down 50%-90% while the broader stock market is only down 10-20%.I could potentially see something similar happen in the real estate where a travel pullback pulls the real estate market as a whole down a little bit, but the most dependent/bubbly locations where people only buy because of the travel market are effected far more.Again, I don't think it will happen, but it is far more plausible than people give it credit for. 

While I have never considered just buying one property to rent out, all the fundamentals of that choice are there (not enough senior housing for the spike we will see when the next generation reaches retirement, typically higher rents, etc.). 

And you can meet the timelines for each sale it is perfectly fine to sell the two and combine them into one replacement.It's called a consolidation exchange and is a fundamental 1031 process.  

Lot's of great economic fundamentals, but the reality is that the annual maintenance on these houses is already killing me even though the properties are clearly appreciating.

I personally think paying rent breaks the fundamental rules in my mind Ha ha ha.  

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I found it through realtor.com web site; I used my realtor friend to make an offer well below asking.

Buying right also means buying a property where the fundamentals generally make sense now and will continue to get better in the future.