@Joel Schiffer
Joel-
These are all exceptionally good questions. First, I would like to recommend a book by @Dave Foster. He can tell you how to get the book I personally have read over 3 times. It has so much information that taking in all the information in one reading is difficult. It is not easy to decide on the best way to proceed. I am in my sixties and reducing my properties by selling out my duplexes in Springfield MO. There has been a significant increase in property values here. I am buying SFRs that will cash flow the same as my duplexes were. This reduces the number of doors I must manage.
In short, we plan to increase cash flow and eliminate what little debt we have left. Using the 1031 process, we will benefit from not paying taxes and be able to leave our properties to our children who are learning the REI process.
The effortless way would be putting it into DSTs. That is not my first choice but it is passive income (3-5 %)
The market is ok but there are still taxes and the chance of loss. Also, there would not be tax incentives like rentals.
If you plan to exit REI, you should consider the nicer house and rent for 2 years
I think that Dave's Book would give you some more options.
Best of luck with your decision.