Any newbie tips?

I have heard that I should have an LLC for each home but it seems administratively burdensome to have 100 bank accounts and 100 different tax filings, credits cards, checkbooks, etc...

@Michael Smythe thanks for the tip.

You make money and are expected to pay taxes. 

What tax benefits might you receive that could potentially offset some of your tax burden with such high income?

You can run the Osha 30 Hour Course on the background of your computer, obtain acceptable levels of insurance and as long as you don't owe the city of Philadelphia taxes, you can get a General Contractor license in Philadelphia.

I know this is pretty obvious, but have you tried checking the Montgomery County property tax records or the property tax assessment records online for Silver Spring?

The house probably also has delinquent taxes etc on it as well.

Looking for someone with experience willing to mentor me, give me some tips on making calls and closing.

If appreciation on the vacation property is what tips the scale for you, why would you compare it to a C/D rental, which likely has low appreciation but higher cashflow per dollar invested?