I finally decided to close the doors mainly because the unit used was not available anymore, but also because the regulations got stricker and stricker over time.Now, if you want to use your 2-4 as an STR, you need to show proof that you are living in the unit you are renting by sharing a government-issued ID with that exact unit or your tax exemption form.If you have a building over 5 units, it's a bit easier but still challenging ( you can rent up to 25% of the units out for airbnb)...the few people I know that are successful are NOT the owners of the building, but more so the operator of the airbnb unit aka str arbitrage

My concern is whether the city could deny permits for these modifications, such as removing walls or converting a garage, or if they are mainly just concerned with safety and habitability.

The main reason I purchase this property is because I was planning to house-hack.

Wasn't that the main point of the post?

We were originally targeting a September 2022 completion date, but now it looks like the front house will be completed April 2023 and the main mid-summer 2023 for the DADU."

She says she notices it in bed and has to put the bed a certain way (like with head on higher part).This doesn't seem to be enough of a problem where any part is unlivable or that requires immediate attention, but the main jist of this post is, where would I start or what type of business or contractor could I start with to find out about this?

And it was a nightmare mainly because of HOA politics, rules/regulations, etc especially if you want to make certain renovations to the unit.

Mainly because so many of us on this website are significantly younger than retirement age. 

Plus, it's become mainly a renter neighborhood as more out-of-state investors poured in.

The main disadvantage of the tax foreclosure auction is that you will be competing with other investors for the property.