Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion

Specific milestones meaning drywall hung, taped and mudded, or all walls/ceiling/trim painted or Final inspection completed and Certificate of occupancy issued.  

A large portion of your net worth will still be staying tied up in the stock market even after selling much or all of your brokerage account holdings to invest in real estate.

And the structure/foundation will be inadequate by today's standards, but unless you're in an earthquake zone, that ain't a big deal either.....

I feel inadequately equipped to offer perspective.

Then you can take distributions on the cash over time or all at once.

I would look for 80-120k houses. that need some cosmetic updating. put 10-30k into them and get them rented and refinance some or all of your cash back out and do it again.

If you did pass one of them or all of them did you ask for any money towards fixing the issues?

What that means is the seller will pay all liens of record at settlement to give you free and clear title at settlement, and depending on the type of warranty deed (special vs. general), that the seller will defend your title against certain (or all) claims after settlement. 

I have no desire to give this job to a bad contractor who does an inadequate job, so in my head I figured it's best to just stay the course.