If there is something that the appraisal will uncover then you might lose your EMD. 

I just read all the BP posts I could find related to the Section 121 exclusion ($250k/$500k capital gains on primary residence) and I uncovered two issues that make me want to sell our AK house soon.#1:   I can only use the 121 exclusion once every 2 years.   

I understand it varies by county but I assume I can just contact the county via phone, email, or online portal.Do you know of examples of what an official title search could uncover that I'm likely to miss?

Curious to know how you managed to blend both practice. and any advice would be appreciated.

Unless HUD wants to provide me a written guarantee that my lawyer tells me protects me and will cover any damages from any lawsuit on an uncovered ESA then the tenant is not renting my units if they have an ESA that my insurer will not cover. 

Jeff will also say that you should know REI from a fix and flip or LL vantage before investing in notes (Jeff, forgive me if I'm incorrect and excoriate as required....I never want to put words in others mouths) but, if you can evaluate the underlying collateral accurately, and are willing to learn about notes and buying notes at a discount, then REI note investing may be the perfect blend between stock market-ish and REI returns that fit your lifestyle and goals. 

Does anyone have recommendations on some good question(s) to ask that might help me secure the deal or uncover more about why they’re selling, what price they’re looking to get, what’s “wrong” with the property, etc.

It might not be "fun" but taking a 4% return on Property #1 knowing that it will enable you to raise a blended average return over time it's exactly bad!  

However, I can still budget for a worst-case scenario if something is uncovered that wasn't anticipated or if the job takes a little longer.

I think both of your responses blend together well in terms of learning the PM business as a whole and learning how property manage and successfully run a business.