As a Condo Owner, you should absolutely make the time to attend several regular Board meetings each year, in particular at budget time, but also two or three times over the year (depending on how often they meet) so you can participate, ask questions, and observe.

My first observation is that I don't believe the numbers the seller is giving you.

I think your initial observations are correct. 

- What trends have you observed in the area over the last decade?

It's important to observe city STR regulations and make sure the property is eligible.

I have never had tenants decline to rent due to having to sign a lead paint disclosure,If you know there is lead paint, observe safety precautions when doing rehab work - the paint will not hunt you down and hurt you, you have to eat it or grind it up into dust and breathe it.

Majority of appraiser's 1) Can't identify a foundation problem if the foundation fell on them lol2)  Wont disclose something observed with the foundation since a foundation inspection is far beyond the appraiser's scope of work and expertise in order to produce credible assignment results per USPAP3) Somehow if they find out from you or god knows where that there is structural damage, it will be dismissed if you can show it was repaired if you do decide to repair it4) I know long term BRRRR investors that buy homes with foundation damage all the time with the intent to hold for long periods of time and address it later on....5) If you plan on flipping to an end buyer soon then this can come back to bite you.

Of course you can find both on each site but that is my general observation.

It's been my observation that in most (if not all) counties, the courts want to see proof of notice to terminate - which is typically either a "X day notice to pay or quit" or a "X day notice to remedy or quit".  

It's not their box we are talking about, it's the box of the observer.