Cash flow decreasing on Class A because I don't do large rent increases on my great tenant (maybe slightly under market rent) and large property tax increases. 

The information contained in this post is not to be relied upon.

These special assessment were thousands of dollars, and there was no sufficient reserves from the monthly fees to cover these large biggers, so the owner were required to cover the shortfalls out of pocket, what a great way to ruin your cash flow and ROI.There are benifits to condos, including tennis courts, playground, swimming pools, club houses, and fitness facilities. 

We had our wedding in the back yd, grew the family and added onto the house making it roughly 1600 sf 3 bed 2 bath.

Here is a list of why adding ADUs in my CA market is typically a poor RE investment:1) The value added by the ADU addition is often significantly less than the cost of adding the ADU.

Passive Pockets, Meta (FB/IG) ads, local meetups are good places to find groups.2.

I added value through great management and a focus on delivering an exceptional guest experience.

Think that adding overhead heaters in the area of hot tub will solve the problem in colder months.

You said, why, not what.Because there is going to be a large drop in licensees.

Whether you should take a retirement distribution or not depends on several factors1) How much do you value the freedom/flexibility to ues the money NOW compared to when you are 60 years old.2) What type of return can you get having cash vs investing in an IRA / SDIRA.If you can make a 1% - 2% better annual return in your personal name, it may make sense as the added return will pay for the penalties over a couple of years.I personally cashed out of my retirement account back in 2016 and it was the best decision I made.