I didn't find any challenge finding quality tenants by posting on FB marketplace, roomster, roomies, basically all of the websites. 

He's a really smart guy when it comes to supply, demand, rent control, and overall investing

At that time and place if you carried a sword you found yourself being challenged to duels.

I spent considerable time pulling comps and estimating fair market value, but given the unique features of this property, it was challenging to reach a confident valuation.

Zillow Research and Redfin Data Center are also good resources to check property trends.Finding Deals: LoopNet can be a bit challenging for finding "undiscovered" deals, as most listings there are already on the market.

First of all, as someone very very very remote from IT/tech world, it's going to be quite a challenge for me to get my site SEO optimized.

Challenges?

Challenge in going alone is knowing all the information and how to get to it. 

@Roopesh KrishnamoorthyFinding cash flowing SFR is going to be a challenge (especially since you are looking for a primary at this point) and if you leave (H1B lottery) then do you plan to continue to fund any shortfall from India?

Challenges?