After some research online, I am reading that the cost per square foot on a gut renovation of this nature in Stamford CT is anywhere from $150-$350, which is ultimately not very helpful, because at $150 per sq ft, this is a very appealing project with a total profit of ~$175K (46% ROI) and at $350 per sq ft, it very much isn't, because it would be a net loss of 83K (haha).QUESTIONS:What can I do refine my estimate a bit given that I am not allowed to a formal inspection on the property? 

Another variable in the amount of rent that a Section 8 tenant can pay is HUD limits their rent payment based on the amount of their income. 

Quote from @David Brooks: I've received advise that our friendly STR loophole can not be used to characterize STR income/loss as non-passive on a California tax return. 

Do we just have a written agreement between father-son (is there a viable legally recognized agreement online to use)?

I'm shopping and ordering online given that my apartment is out of state and I'm flying in to set everything up.

It is now treated as a former passive activity and those prior losses can only offset income from that same activity going forward. 

Consider starting with house hacking to reduce housing costs while learning property management, or explore mid-term and short-term rentals for steady or higher income.

In online forums, the danger I've experienced is the "national" effect. 

This could reduce your taxable income in those years.Your decision depends on your long-term strategy.

You would just be using the property's income to qualify.