Have this going on with a property now where I am renting just a room to a mid term tenant while we are out of town.

How about making it a mid-term rental?

Philadelphia, particularly the better neighborhods remain great value relative to its mid atlantic counterparts.

The only way we were able to buy a home that would produce cashflow in the future was to buy a home with a loan that was taken out between early 2020 and mid 2022.I don't know if you are placing a large down payment or paying in cash to allow for a better chance to ensure cashflow, but if you are using financing I would highly recommend buying your next home as a primary with an assumable loan. 

If you have a high salary and a secure profession maybe you take the risk on a break even property that is going to appreciate and rents go up (I would not put 40% down to do it) but if you are at the mid to lower range that negative cash flow can push you over the edge.

Paid $30,000 for their "Six Figure Land Flipper" 6 month course to start mid-June.

Hi Brandon, depending on the location you could probably cash flow more than that as a short term rental or mid-term rental.

If they lease between November and mid March you are adding vacancy to find the right person at an optimum price so I would  make sure they end leases and set new expirations in the spring to early fall to ensure that.Back to asset class though think of that because if the preexisting tenant is dirty and destructive not only do you need to pay to fix the stuff their deposit won't cover but you also might have 2 to 4 weeks of vacancy before you can even start to lease it. 

And  I am  like DUDE these guys prey on those that dont know what they dont know my Dad taught me about the fake lenders way back in the mid 70s ..

Many investors from California, are investing in the mid-west because of the yearly returns making more sense in these lower priced markets.