take Oakland and Oakland Schools  Piedmont Borders Oakland if you cross one street into Piedmont with Piedmont schools the values literally DOUBLE for the exact same house.  

This single-family home sits on a 1.5-acre property and is 6,400 sf, six bedrooms, five bathrooms, a pool, a hot tub, and an expansive balcony.

My pricing software automatically discounts weekly and monthly stays, good to know so I am not double discounting, if I am affected at all.

Initially, I planned to finish the attic, add a bathroom and bedroom, and create a first-floor master suite, turning it into a 3/2.

I would double check with the city, remember, trust but verify.Here's a link https://www.phila.gov/services/permits-violations-licenses/a....I'm doubtful that this scope of work doesn't require a permit.I do my jobs with permits because I'm risk adverse.Its easier to ask for permission than beg for forgiveness.Best of luck 

Some will cost more than expected, some less.If you are worried your calculations are too conservative, add 25%, 50%, or double them.

Using a double headset you can call two numbers at once and a predictive dialer can call more.  

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

It a 2 bedroom townhouse with 2 queen size beds.

As far as HML's go, they will double check your deal to make sure the numbers work (for both of you) as they are not going to lend on a property that they have not vetted.