Hey James,Builders don’t push HOAs because they’re worried about buyers loving fees—they do it because HOAs protect the long-term value of the whole subdivision, which makes their job selling homes easier.Here’s why:Property values stay consistentHOAs enforce rules about lawn care, paint colors, parking, etc.That means the house someone bought for $450K doesn’t end up next to one with a car on blocks in the yard six months later.Builders can hand off responsibilitiesRoads, stormwater ponds, shared amenities—without an HOA, the city might not maintain them, so the builder would be stuck.HOA takes that off their plate.Financing gets easierLenders often like HOAs because they reduce risks tied to neighborhood upkeep, especially on big new developments.Price opticsDropping the HOA doesn’t feel like a “discount” to most buyers; lowering the sale price does.

It sounds like you’re already taking the right steps to educate yourself before taking that leap.When it comes to building your team it comes down to your own due diligence.

If this is indeed your question, then it's not a great question.

This in theory would allow you to purchase the home you have under contract in one room, assign it and have your assignee sign in the room next to you. 

I can roll over the depreciation to offset my gains later on, but is there any benefit for me to do cost segregation and maximize my early depreciation if it's not going to matter until I sell?

If you want to do MTR or LTR do it.

When the numbers pencil out and there’s some experience or support behind the scenes, it’s not about risk, it’s about momentum.

Condos can be flipped, as any flip it's all about numbers.

What information do you need to gather when you're trying to analyze if it probably works as a short-term rental?

If you can't do it yourself, it may be worthwhile to pay an accountant or tax expert to run the what-if analysis for you.