Running water through it? 

In the long run it would save you $. 

Quote from @Lucy Ahl: Who do they have to answer to or do they just get to run amok and do whatever they want, no matter how unreasonable?  

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.

Typically, I run a current income/expense column next to a ProForma column to show potential value add opporunties.I agree with @Robert. 

Again, if your $250k is true, and includes all the electrical upgrades, new plumbing runs, potentially new foundation pour (since I assume the existing garage slab is not capable of supporting a new two story house), I am guessing since I don't know the market, but assume you will have a lot of equity by completing the project.

I figured my network of people I help/work for, will help in the long run. 

I had my broker run comps in the immediate area for rent and ARV.

Multi-story CBD office buildings in downtown urban areas are the product that is struggling.When you say temporary, infrequent use, are you speaking about leasing smaller Executive Offices or running a business similar to WeWork?

Rental properties may be more passive than some other investments... but remember this: You're running a small business.