The listing agent should be able to tell you if there are age or rental restrictions before you even view the home. 

What would yall recommend to be the best strategy to entering real estate at my age.

Someone with one newer aged rental, who has a rather high income, such as a surgeon who lives alone comfortably with a lot of disposable income, could possibly carry less than a Mr and Mrs just starting out, with one rental that they bought as a turnkey in a more downtrodden neighborhood in a different state.

Assuming you "converted" the property to rental 4-5 years ago and you filed for rental applications/permits and have been filing 1040's for that property then you should be good from an age perspective. 

I think you are in the right mind set however with the out of state investing - its much easier in this day and age and NY is not a great place to get started in this type of investing

Fuel for the day: A little English Breakfast aged tea, full fat cream, and, my favorite, raw unadulterated organic honey.

I love helping people and truly do enjoy my job, but I am already at a young age topped out for compensation and in this field with insurance reimbursement structure the way it is, I am likely to not move up much at all in the future unfortunately.I have always loved personal finance and after accruing ungodly amounts of student loans and navigating paying them off all while efficiently investing in the stock market as well as now real estate I have not only realized how strong my interests are in this area but also my personal skills align in financial planning and personal finance.

Age of construction may not be a huge issue if it has good bones and can benefit from a fairly cost efficient "In & Out" remodel.What is stopping you down payment?

Some also factor for the age of drivers, driving record, prior losses, etc. 

The main issue with many Philly homes is the age these properties were builtThis give you 2 main concerns:1.