GFCI outlets don't always fit into old elec boxes because the GFCI are physically much larger than regular outlets and old boxes are usually very small.

However, fixed costs when vacant… The space is on one of the busier intersections but the location is very good in proximity to restaurant (across street), party store walkable, beach park short walk.

The WFH/Uber trends might be changing that, but metro access and DC proximity are still selling points for now. 4.

This is mostly because you are dealing with people that buy into a community to put down permanent roots and don't want to be transient (like renters) and are living in very close proximity with shared walls. 

What would be the best arrangement to eventually acquire the home, while also giving them the security (cash from the sale of their home), a close proximity to friends/family/grandchildren and a smaller home that maintenance would be cared for? 

You could look into owning physical gold and silver, which is a very safe investment, despite what the fluctuations in the market may lead one to believe. 

Also the proximity to the theme parks, generally speaking, is better with condos and townhomes.

If you need a physical local person, I would join local STR Facebook groups and ask who others use.  

With hundreds of cat rentals over the years, I've never had to spend much to repair physical damage.The real damage from cats is odor.

Very well said I think the only thing that I would add to this conversation is that people need to spend more time understanding the mental side of being successful. having a certain amount in your bank account does not deem you to be successful and if you don't start working on it from the very beginning you'll never know when you reach it and it's not like you popped through a glass ceiling and you're on the other side and now you think that you're going to flip a switch and enjoy your life part of doing this is learning and enjoying the journey that you're on not just trying to get to the destination thinking you'll be happy at that point.You have to become a successful person mentally before you ever will financially or physically