For the District of Columbia, is there a template or any advice on what works to challenge property tax assessment increases?

If you have a strong Metro it can make up for a lot of other less appealing factors.

The idea of buying one multi deal is very appealing to me for a "one purchase replacement" of what I currently make monthly now.

Quote from @Bruce Lynn: House hack, but it's not escaping the rat race, just trading one race for another.This is a great point but not necessarily a bad thing :)Trading the 9-5 rat race for independence as a rental property owner really appeals to me!

While property managers would tend to only look for paint overspray and curb appeal.

Storage space will always appeal to people, especially bigger families with kids.

However, I totally get that other states like Wyoming offer some appealing perks like anonymity and lower costs, as @Joshua Davidson mentioned.

Quote from @Josh Mahan: Part of the appeal for me personally is being able to use an old 401k to fund.

Not all areas are equaling appealing from a buy and hold lens.

It must be move-in ready, bright, and appealing, with as much of a like-new feeling as possible.