This tells me that I can either: a) buy a $200k property but incur a negative monthly cash flow of roughly $100/month (because of the large monthly payments) or b) buy a cheaper property in a good area that requires a bit of repairs. 

If everything else nearby is cheaper, no one will be willing to rent from you or bail on their leases early.  

My other option is to use that space to do a cheaper (no kitchen/bath) addition that ties in w the house for an upstairs media room/office and adds 500sq' to my house size.I know there are a lot of details I'm leaving out about my personal situation - but just a general answer is all I'm looking for from a more seasoned investor than myself.

Francisville, North Broad, and Brewerytown are north of the city and are on the cheaper end, they are close to the nicer Fairmount and Art Museum Neighborhoods.

One point of view is if renting becomes cheaper than buying the price of condos for sale will also level off.

When you are buying you want a higher cap rate since it makes the property cheaper (dividing by a larger number).Using the numbers you provided above, you get a very low cap rate based on asking price.

If your going to pay a plumber to replace the cartridge, then yes the warranty company would probably be cheaper. 

A cheaper truck would get you independent quicker, albeit with less frills.18 months is not enough time to park money in an index fund (at least not a stock fund).

Andrew Johnson you can also go to a used jeep dealer and see what they would give you for a trade to a cheaper car from their lot.

The following are the options what I currently see 1) Purchase quality property for rental and worst case I will be paying Rent + mortgage (~50% of income)2) Purchase a much cheaper property...but not feel comfortable with its quality (~35% of income in worst case)3) Wait a couple more years to get mortgage much lower.