If a property is considered uninhabitable, the Landlord must provide the tenant a hotel at no cost to the tenant (this much is a preexisting requirement).

I was not sure on the way to decide on a price, nor to estimate the repair cost.  

Say I have $35,000 in a HYSA that generates $150 per month in interest. If I invest that money into a rental property that breaks even, wouldn't I actually be cashflow negative $150 per month now that I'm not getting ...

So you’ll be deducting 1/27th of the cost per year.

The only way to 100% verify is to cut a 2' x 2' patch of drywall in the suspect area and see what it looks like.

Either one would be our primary residence, so down payment and closing costs are fairly the same.

Meaning, when it came time to actually sell the property, (for tax purposes) the cost basis of the property was reduced by the full depreciation amount, reducing the amount of capital loss (which could be used to offset more profitable investment).5.

It is challenging but we committed to going there every 4-6 weeks and having a great team on the ground ( will cost you some extra money) but they are the difference in having issueswe have one of the best cleaners in the area and our guy that cleans the grills does all my light maintenance and guest interaction if I need it(pets, too many guests etc.)3-4 hours would be a dream and you can definitely do it but you have to commit to going there every 4-5/6 weeks In my opinion because there will be things you need to address or upkeep- this is obviously only if you decide to self manage. 

Could you provide granularity on costs segregated and potential assets?  

So they cut the values in half and then raised the tax rate 90%.