hi @Nicholas Carelli,
I'm 26 and I absolutely can relate with the getting old feeling ... I'll be 27 in November!
First and foremost, congrats on being able to save like a boss (Rick Ross Voice)!
I buy and sell in philly now and condo's are awesome and then they are not.
I think your plan is great, and the only reason I feel this way is because you have a friend that will be helping you out with expenses (however I want to warn you against renting to friends & Family).
Things to consider will be:
1) Will you still be able to save once you buy?
2) Will you still be able to save EVEN WITHOUT your friend to help split the bills.
Condos are convenient but you pay for the convenience, all of them will have a monthly condo fee on top of your PITI (principle, Interest, Taxes, and Insurance) and some will have a one time fee for you to enter the condo aka a "Contribution Fee". One good thing is that some condo fee with cover your insurance, the exterior of the building so you only have to worry about your unit interior with greatly decreases what you pay for in insurance. From my experience, if possible, you're better off looking for a house, something super nice. This way you avoid the condo fee in all. and if you can't find a 4 plex ... why not do a duplex or a triplex, something smaller.
But if you're set on grabbing a condo ... the get at it! Look for something ugly and under priced and grab it up, and do light renovations as you move along. Maybe a new kitchen this year, new baths the 2nd year, new hardwood floors the 3rd.
I so badly wanted to be in a condo downtown and in the mix of it all.
But I settled for a 4plex in west philly about 3 miles outside of downtown because the numbers made sense ( 4 units, 2 bedroom 1 bath, and each can rent $750-850/m so very very happy). It's is bad shape but I will renovate it and take it from there. I settle Aug 31st (fingers crossed though, you never know what could delay a settlement).
In closing, there's no right answer! It's honestly what you want to do but make sure you're realistic and consider everything before you make your move. The reason I didn't go with a condo is because I knew it would really slow down my ability to save. and without my savings I wouldn't be able to get to property #2, and property #3 and property #4 and so forth. My goal now is to get to net $6,000 cash from my rentals and then I can honestly go where ever I want, downtown or not. but until then, I will try to sacrifice!